JPH0564391B2 - - Google Patents

Description

[Detailed description of the invention]

[Field of the Invention] The present invention relates to a method for recording and retrieving chemical reaction information using a computer. More specifically, the present invention relates to a method for recording and retrieving chemical reaction information using a computer. It relates to a processing method for recording and searching to facilitate consideration of similar compounds and reactions, and research on methods of synthesizing new compounds with similar chemical structures. [Technical background of the invention] In recent years, with the development of computers,
Various methods have been proposed and are being used to record structural information on chemical substances, especially organic compounds. A huge amount of organic compounds and organic chemical reactions have been studied and elucidated to date, but it is possible to effectively use this known information to quickly search for known chemical substances or chemical reactions. Furthermore, it is desired to find a method for synthesizing new substances having desired properties. To this end, computers can process chemical formulas (i.e., computers can make logical judgments) instead of conventional chemical structural formulas, which are easy for engineers to understand, as a form of expression for chemical substances and chemical reactions. There is a need to develop and utilize forms of expression (that are possible). WLN (Wiswes) is the recording method for chemical substances.
Typical methods include linear notation (such as ser Linear Notation) and methods using join tables.
Feldmann, E. Hyde (Eds): “Computer
Representation and Manipulation of
Chemical information” (John Wiley and
Sons, New York, 1974) [Wipke, Heller,
Feldman, Hyde (ed.): Computer Representation and Handling of Chemical Information (Jon Willey and Sons). For example, a connection table is a table that lists the type of each atom in the structural formula of a chemical substance, the atom to which it is bonded, and the type of bond. It has the advantage of being able to search for substances on an atomic basis. Methods for recording information regarding structural changes (chemical reactions) of chemical substances have also been proposed, but no satisfactory method of expression has been known so far. For example, one way to record information about chemical reactions is to use reaction codes.
Specifically, J. Valls, O. Scheiner: “Chemical
Information Systems”, E.Ash, E.Hyde (Eds),
(Ellis Horwood Limited, 1975) p.241-258 [Barr, Scheiner: "Chemical Information Systems", edited by Atsushi, Hyde (Ellis Horwood Company)] MALobeck, Angew.Chem.
Intern.Ed.Engl., 9 , 578 (1970) [Robetsk, Angewante Hiemi International Edition in English], and HJZiegler, J.Chem.Inf.
Comput.Sci., 19 , 141 (1979) [Ziegler, Journal of Chemical Information and Computational Science]. This method has a drawback in that it cannot record new chemical reactions when they are discovered, since the viewpoint of chemical reaction expression is fixed. Another drawback is that structural information on chemical substances and information on changes thereof are recorded in separate formats, making it impossible to perform effective information retrieval. Separately, a recording method devised from the standpoint of designing synthetic routes for chemical substances is also known. for example,
E.J.Corey, R.D.Cramer, W.J.Howe, J.Am.
Chem.Soc., 94 , 440 (1972) [Kohli, Cramer,
Houe, Journal of America, Chemical Society], I.Ugi, J.Bauer, J.Braodt,
J. Friedrich, J. Gasteiger, L. Jochum, W.
Schubert, Angew.Chem.Intern.Ed.Engl., 18 ,
111 (1979) [Ugi, Bauer, Braut, Friedrich, Gasteiger, Joetschiam, Schubert, Angewante Hiemi International Edition in English]
There is a method described in However, this method is not suitable for recording individual chemical reactions. [Summary of the Invention] An object of the present invention is to provide a novel processing method for storing and retrieving information regarding structural changes, including the ionic structure of chemical substances, using a computer. The present invention also provides chemical reaction information that integrates information regarding structural changes including the ionic structure of chemical substances.
It is also an object to provide a new processing method for storing and then retrieving information in a representation form that can be processed by a computer. A further object of the present invention is to provide a novel processing method for storing and retrieving information regarding chemical substances having an ionic structure based on chemical reaction information. Furthermore, another object of the present invention is to provide a novel processing method for recording and storing information regarding chemical substances having an ionic structure based on chemical reaction information in a representation form that can be processed by a computer, and then retrieving the information. It is something to do. The present invention is a process of topologically superimposing the structure of a starting material and the structure of a product in a chemical reaction that produces at least one product from at least one starting material; (1) Bonds between nodes that exist in common in the starting material and product material, (2) Bonds between nodes that exist only in the starting material, and (3) Bonds between nodes that exist only in the product material. Obtaining bond information in which the bonds are differentiated and ionic structure information regarding the substance; Based on the above bond information and ionic structure information, an imaginary transition structure containing charges that expresses the structural change of the substance in the chemical reaction. , or a step of creating a bonding table containing information about each node and charge, a binding partner node or charge that binds to the node and the charge, and the bond between the node and/or the charge; the above imaginary transition structure or bonding table; A step of recording and storing the information in a recording medium attached to a computer; and from the recorded imaginary transition structure or connection table,
Chemical reaction information, including the step of searching for the structure of a starting material, the structure of a product, or a partial structure thereof by searching using the above search conditions for bond information or ion information, or a search condition that combines these information; It is in the recording/search method. The present invention also provides a step of topologically superimposing the structure of a starting material and the structure of a product in a chemical reaction that produces at least one product from at least one starting material; (1) Bonds between nodes and/or charges that are present in common in the starting material and product, (2) Bonds between nodes and/or charges that are present only in the starting material, and ( 3) A step of creating an imaginary transition structure containing charges by distinguishing nodes and/or bonds between charges that exist only in the generated substance; A step of recording and storing the above imaginary transition structure in a recording medium attached to a computer. ; Then, from the displayed imaginary transition structure, by computer processing, only the bonds between charges are deleted to obtain an imaginary transition structure displayed as ionic bonds, or only the charges and the bonds between nodes and charges are deleted, and obtaining an imaginary transition structure represented by a covalent bond by representing the bond between nodes corresponding to the bond between charges. Furthermore, the present invention provides a step of topologically superimposing the structure of a starting material and the structure of a product in a chemical reaction that produces at least one product from at least one starting material; Between the structure of the product material, (1) bonds between nodes and between nodes and charges that exist in common in the starting material and product material, (2) bonds between nodes and between nodes and charges that exist only in the starting material. , and (3) a step of creating an imaginary transition structure by ionic bond representation, which distinguishes the bonds between nodes and between nodes and charges that exist only in the product substance; A step of recording and storing the recorded imaginary transition structure; and removing bonds (3) between nodes and between nodes and charges that exist only in the generated material by computer processing from the stored imaginary transition structure to obtain the starting material expressed as an ionic bond. or obtaining the structure of the product expressed as ionic bonds by deleting bonds (2) between nodes and between nodes and charges that exist only in the starting material; There is also a method for recording and searching. In the present invention, the term "imaginary transition structure" refers to structural changes of substances involved in chemical reactions into three types: bonds that exist only in the starting material, bonds that exist only in the product material, and bonds that exist in common to both. It refers to a two-dimensional or three-dimensional structural diagram that is differentiated, and in particular, an imaginary transition structure containing charges is called a ``double imaginary transition structure''. In addition, a "bond table" is a list consisting of combinations of types of nodes and charges, partner nodes or charges that bond to the nodes and charges, and types of bonds between these nodes, between charges, and between nodes and charges. It is. First, according to the method of the present invention, chemical reaction information can be automatically obtained as an imaginary transition structure and/or a bond table via a computer based on information regarding bond changes and ionic structures of substances in chemical reactions. I can do it. In other words, chemical reactions basically use these imaginary transition structures and bond tables to provide simple expressions for the bonds between nodes (nodes) consisting of atoms and atomic groups and the charges associated with the nodes. Since the bonds between nodes in the reaction system are expressed separately into the three types mentioned above, it comprehensively contains information about the substances involved in the reaction in addition to the chemical reaction itself. Therefore, these registration formats are extremely superior to various conventional registration formats in that they can simultaneously record and store both chemical substance information and chemical reaction information. In particular, the imaginary transition structure allows chemical reactions to be expressed in a form that is visually familiar and easily understandable to engineers in accordance with conventional structural formulas and three-dimensional structural diagrams of compounds. Also,
According to the bond table, chemical reaction information can be recorded and saved on a recording medium attached to a computer without requiring a large capacity. In the present invention, if the obtained connection table also includes information about the position coordinates of each node, it is possible to arbitrarily convert between the structure diagram and the connection table, and any Chemical reactions can also be displayed and recorded on a display. In addition, for example, the bonds between each node can be represented by a pair of numbers (a, b) [where a is an integer representing the bond multiplicity in the starting material, and b is an integer representing the change in bond multiplicity in the chemical reaction. ], it is possible to display not only individual reactions but also a plurality of consecutive reactions (multi-step reactions) in one combination table on a display device attached to a computer. Therefore, any intermediate reaction and series of synthetic reactions can be easily represented using the bond table and the imaginary transition structure. In addition, in the double imaginary transition structure and bond table including charges according to the present invention, not only bond changes between nodes in a reaction system but also charges at nodes can be expressed in the same way as nodes. Structural changes can also be easily expressed in a form that is easy for users to understand without taking up body volume. In other words, the chemical reaction information of the present invention can easily include information regarding charge (ion information), and even when ions are involved in the reaction (ion reaction), changes in the ionic structure of the substance in the reaction system can be easily included. can be described accurately. For example, a double imaginary transition structure can be represented by two spaces: a composite space containing the node and a charge space containing the charge corresponding to this node, making it easy to visually understand the contribution of charges (ions) to the reaction. . Second, by performing simple graphical processing or arithmetic processing on this double imaginary transition structure containing charges via a computer, we can arbitrarily change the structure of the substances involved in the reaction by ionic bonding or covalent bonding. It is possible to provide reaction information and substance information in a form that is more easily accepted by users. Third, we focused on distinguishing bonds based on the double imaginary transition structure and bond table containing the above ionic structure information, or based on the imaginary transition structure displayed with ionic bonds obtained by processing this. By performing simple graphical or arithmetic processing via a computer, information about the chemicals involved in the reaction can likewise be obtained in the form of (double) imaginary transition structures or bond tables. In other words, only chemical substance information can be extracted from chemical reaction information. In addition, when chemical substance information is obtained in the form of a structural formula (two-dimensional structural diagram) or three-dimensional structural diagram, it is easier for engineers to visually understand, and it is similar to the way compounds are normally represented. Since there is such information, there is an advantage that the information can be displayed directly on a display device such as a display attached to a computer and used. When chemical substance information is obtained in the form of a bond table, it is easy to compare and match chemical reaction information also expressed as a bond table, and the magnetic recording medium attached to the computer does not take up a large capacity. It has the advantage that it can be recorded on electromagnetic recording media such as optical recording media, magneto-optical recording media, or recording media that utilize light. The imaginary transition structures and/or bond tables obtained for chemical reactions and substances involved in the reactions can be further recorded and saved in a computer storage medium, or recorded on blank paper or displayed on a screen such as a cathode ray tube. can. Further, by utilizing the method of the present invention when recording and storing chemical reaction information and further chemical substance information, the information can be easily processed by a computer and does not require a large storage capacity. Since chemical reactions and chemical substances can be easily registered on the recording medium, it becomes easy to accumulate and manage this information. In addition, based on registered chemical reaction information and/or chemical substance information, information searches regarding chemical reactions and chemical substances can be carried out quickly and efficiently using computer processing. In each individual research, it is possible to shorten the time required to collect information, investigate, etc., and increase the density of information obtained, allowing research to proceed efficiently. In addition to these advantages, by using the chemical reaction information and chemical substance information obtained by the method of the present invention in combination, it is possible to analyze chemical substances, which is highly desired by engineers involved in drug manufacturing. Structural analysis, molecular modeling, heuristic analysis of organic synthesis
synthesis). moreover,
Search for substructures of chemical substances, structure-activity relationships, automatic structure determination of unknown compounds, and prediction of reaction mechanisms and reaction products when complex compounds are reacted under certain conditions (mechanistic evaluation of
(organic reactions) can be carried out within a sufficiently practical range in a short period of time. [Specific Description of the Invention] In the method for recording and retrieving chemical reaction information of the present invention, first, based on input information regarding bond changes and ionic structures of substances involved in the reaction,
An operation in which the structural changes of a substance during a chemical reaction are recorded in the form of an imaginary transition structure containing charges and/or a bond table on a recording medium attached to a computer, and then displayed on a display device attached to the computer such as a display. will be carried out. The method of the present invention will be explained using an example of an ammonium ion production reaction. Chemical reaction example 1 Ammonium ion production reaction This chemical reaction is It is expressed as For all starting materials (fibers) and product materials (product system) involved in the reaction, the nodes and the charges associated with the nodes can be taken as follows. Original system R ₃ N Cl ^- H ⁺ production system

[Formula] The original system (starting material group) and the product system (product material group) expressed by this normal ionic structural formula are superimposed topologically, that is, in the same phase.
Bonds between nodes, bonds between charges (ionic bonds)
and bonds (ions) between nodes and charges: (1) bonds that exist in common in the starting material and product material, (2) bonds that exist only in the starting material, and (3)
Distinguish between any of the bonds present only in the product substance. Therefore, in the present invention, "topologically superimposing" refers to combining nodes appearing in the structure of the starting material and nodes appearing in the structure of the product material by matching them. Then, information regarding the types of these nodes and charges and the coupling between the nodes and/or charges is input into the computer. Specifically, information regarding the bond between each node and/or charge, such as "The bonding relationship between R ₃ N and H is (3)", can be input individually as text information in an interactive format.
When inputting in the form of letters, numbers, etc., positional information such as two-dimensional or three-dimensional coordinates of each node and charge can also be included. As a result, A structure containing charges represented by is obtained. Here, a space having nodes such as R ₃ N will be referred to as a "synthetic space", and a space having a charge such as (+) will be referred to as a "charge space". Also, (i) the symbol - represents a bond that exists in common in the starting material and the product, (ii) the symbol + represents a bond that exists only in the starting material, and (iii) the symbol... represents a bond that exists in the product represents a bond that exists only in In the present invention, the above DITS1 is converted into double imaginary transition structures (double imaginary transition structures).
(hereinafter abbreviated as DITS). In other words, a double imaginary transition structure (DITS) is a structure in which the structure of a starting material including an ionic structure and the structure of a generated material are topologically superimposed, and the bonds between each node and/or charge are formed by the above (i) to ( It refers to two-dimensional or three-dimensional structures classified into three types (iii). In the present invention, all atoms contained in the source system and the product system may be used as nodes of substances involved in the chemical reaction, or atomic groups such as functional groups such as methyl groups may be used. Further, when expressing a chemical reaction, it is possible to partially omit some nodes appearing in the original system and the production system, and this is also included in the present invention. In the double imaginary transition structure (DITS) according to the present invention, the distinction between the three types of bonds is not limited to the symbols (i) to (iii) above; for example, numbers (1, 2, Any means may be used as long as the user can make a judgment using the five senses and can be processed by a computer, such as simple text display such as 3) or color-coded display (black, red, green). In the following, in the present invention, (i) a bond (symbol -) common to the starting material and the product substance will be referred to as a "colorless bond" or a constant bond (par-
(ii) A bond that exists only in the starting material (symbol +) is called an "out-bond"; (iii) a bond that exists only in the product material (symbol...) is called an "in bond". ” (in-bond), and out-bonds and in-bonds are collectively called ``colored bonds,'' and these three types of bonds that appear in imaginary transition structures are collectively called ``imaginary bonds.'' Make it. Specifically, Table 1 summarizes the types of bonds that appear in the imaginary transition structure of the present invention. Note that in Table 1, the horizontal numbers mean indicators of the inflow and outflow of bonds.

[Table] In Table 1, for example, the bond represented by the symbol "..." is a single in-bond, and can be represented by a pair of numbers (0+1). Here, 0 means that no bond exists in the original system before the reaction, and +1 means that a single bond is present in the product system after the reaction. Similarly, the bond represented by "+" is a single out-bond and is represented by (1-1). This means that single bonds have disappeared in the system. In addition, the bond represented by (2-1) is a double bond singly
cleaved) and is written as "±". Thus the type of join is also a pair of numbers:
(a, b) [where a is an integer representing the bond multiplicity in the starting material, and b is an integer representing the change in the bond multiplicity in the chemical reaction], and this can be expressed as ``complex bond number ” (complex
bond numbers) or imaginary multiplicity
multiplicity). In addition, (a,
In the notation of b), the comma (,) may be omitted.
According to this notation, even if the connection multiplicity is two or more, it can be expressed concisely. In addition, it is particularly preferable for storing records of chemical reactions because it does not require much storage capacity and can be directly processed by a computer, and is a preferred expression method for creating the bond table described below. Alternatively, each node and the type of charge,
The bond between each node and/or charge is a constant bond,
Based on the input information about bonds and charges with out- or in-out bonds, a connection table is created.
You can also create a table. Table 2 shows the bond table obtained for the above ammonium ion production reaction. Note that the connection table also includes information regarding the two-dimensional coordinates (xy coordinates) of each node.

[Table] As shown in Table 2, the bond table includes all nodes,
Charges associated with a node, its two-dimensional coordinates (node
(1) as the origin, and the charge space has the z coordinate as ∞), a list of all nodes or charges that bond to each node and charge, and the types of bonds between them, listed in order of node number. It is a table. A bonding table can also be created based on the double imaginary transition structure described above. Alternatively, a connection table can also be created directly from information input in the form of a double imaginary transition structure. The double imaginary transition structure and bond table created for each chemical reaction in this way can be registered in a recording medium attached to a computer. These registration formats are excellent in that even if the reaction involves ions, the reaction information is expressed in a format that is easy for the user to understand, and registration is easy. In particular, when the registered form is a double imaginary transition structure, the form is similar to a general-purpose structural formula, so a person who intends to use chemical reaction information can visually understand and judge immediately. Furthermore, if the registration form is a joined table, it does not require a large storage capacity and can be directly processed by a computer. Note that it is of course possible to register a combination of the bond table and the double imaginary transition structure, which is preferred in the present invention. The connection table may also include input information regarding the spatial coordinates of each node, etc., as described above. Furthermore, the double imaginary transition structure and/or the bond table may include information regarding the stereochemistry of each node, etc., if desired;
Various physical property values and spectral information of the chemical substances involved in the reaction; as well as information on the enthalpy, temperature, time, catalyst used, atmosphere, reaction phase, reaction yield, presence or absence of by-products, etc. of the reaction are listed. Good too. If the double imaginary transition structure or bond table registered in the computer contains this additional information, the double imaginary transition structure or bond table can be used as a database for chemical substance structure search systems and chemical reaction search systems. , or an organic synthesis design system. When registering the double imaginary transition structure and/or bond table described above in a computer, a reaction number is assigned for each double imaginary transition structure and/or bond table to facilitate the accumulation, management, and retrieval of chemical reaction information. Alternatively, a reaction name may be registered for each double imaginary transition structure and/or bond table. Next, based on the above double imaginary transition structure, a double imaginary transition structure represented by an ionic bond and a double imaginary transition structure represented by a covalent bond are obtained by the method described below. If we remove the imaginary bonds in the charge space from the double imaginary transition structure expressed by DITS1, we get Imaginary transition structure (ITS) displayed with ionic bonds
is obtained. In the present invention, the operation of extracting ITS based on the ionic bond representation from this DITS will be referred to as "projection of ionic bonds" (hereinafter abbreviated as PI). In addition, from the double imaginary transition structure expressed by DITS1, we delete the charges in the charge space and the imaginary bonds (bonds between nodes and charges) spanning both spaces, and change the imaginary bonds in the charge space between the corresponding nodes. Represented as a bond. In other words, by projecting only the imaginary combinations of the charge space onto the composite space, An imaginary transition structure (ITS) is obtained, which is represented by a covalent bond. In the present invention, the operation of extracting ITS based on the covalent bond representation from this DITS will be referred to as "projection of covalent bonds" (hereinafter abbreviated as PC). The details of ITS based on this covalent bond representation are described in the specifications of Japanese Patent Application No. 177345/1982 and Japanese Patent Application No. 180875/1987 filed by the present applicant. By applying the information processing of the present invention to the chemical reaction information represented by the double imaginary transition structure in this way, the chemical reaction can be displayed as either ionic bonds or covalent bonds, and the user can You can obtain information displayed on either side. That is, it is possible to arbitrarily select any conventional display format depending on the individual reaction or its field of use. Note that it is of course possible to create a bond table corresponding to ITS based on an ionic bond representation or a covalent bond representation from a bond table corresponding to DITS. Next, based on the obtained imaginary transition structure represented by the ionic bond, the starting material and product material for the chemical reaction are obtained by the method described below. Delete the incoming bond (symbol...) from the imaginary transition structure based on the ionic bond representation represented by ITS1 to make it non-bonded. Then, if the remaining constant bonds (symbol -) and outbound bonds (symbol +) are expressed in normal bond representation according to their bond multiplicity, The following structural formula is obtained. These structural formulas represent the original system of the above-mentioned ion production reaction, that is, the ionic structural formulas of the starting materials involved in the reaction. In the present invention, the operation of extracting the original from this ITS is called "projection to the original".
This stage will be called the starting stage (hereinafter abbreviated as PS). Also, remove the outgoing connection (symbol +) from ITS1 to make it non-connected. And the remaining constant bonds (symbol -)
and the incoming bond (symbol...) is represented by a normal bond representation according to its bond multiplicity, then The following structural formula is obtained. These structural formulas represent the production system of the above-mentioned ion production reaction, that is, the ionic structural formula of the product substance involved in the reaction. In the present invention, the operation of extracting the generating system from this ITS is called "projection to the generating system".
This stage will be referred to as the product stage (hereinafter abbreviated as PP). Note that from the imaginary transition structure (ITS2) based on the covalent bond representation, the starting material and the product can be obtained by similar operations. For details, please refer to the patent application filed by the applicant.
60-1853886. Alternatively, for the double imaginary transition structure directly
PS and PP operations (modules) may be applied. Next, by performing PI and PC operations (modules), original systems and production systems based on ionic bond representation and covalent bond representation can be similarly obtained. Therefore, PS+PC (or PC+PS) operation and
By the PP+PI (or PI+PP) operation, the parent system and product system corresponding to the representations of Reaction Formula 1 are obtained, respectively. By performing the information processing of the present invention based on ITS or DITS, information on chemical substances involved in the reaction can be directly obtained and can be used for structural searches of compounds. In addition, chemical substances can be obtained as structural formulas that are commonly used, and can also be expressed as ionic or covalent bonds depending on the substance, making it easier to use as chemical substance information. In addition, from the bond table corresponding to DITS, or ITS based on ionic bond display and covalent bond display
It is also possible to create a combination table for a chemical substance from the combination table corresponding to the combination table, and specifically, it can be created according to the method described in Japanese Patent Application No. 185386/1986 by the applicant. I can do it. Regarding the double imaginary transition structure and the imaginary transition structure based on the ionic bond or covalent bond representation described above, it is possible to obtain a structure in which outgoing bonds and incoming bonds are alternately connected by deleting only colorless bonds. This is called a reaction string. Reaction components can be extracted in a form specific to each reaction type. That is, it is possible to use the registered double imaginary transition structure to extract only reaction signs that are structural expressions specific to individual reaction types, and reaction searches can be further facilitated. In addition, it is also possible to extract only the ring structures (open or closed rings) involved in the reaction. Furthermore, by performing appropriate arithmetic processing on the bonds represented by the number of complex bonds (a, b), it is possible to integrate reactions spanning multiple stages and display them as a single bond table. That is, it is possible to simply display not only individual reactions but also the entire complex reactions such as those in the synthesis of organic compounds, or to extract and display only a part of the reactions. For details on how to further process these chemical reaction information, please refer to the applicant's patent application No. 1974-197463.
No. 60-199920, and Japanese Patent Application No. 60-203690. Therefore, this registered double imaginary transition structure and A join table can be used as the optimal registration form. When performing structure searches, reaction searches, or synthetic design of chemical substances using double imaginary transition structures and/or bond tables containing the above ionic structures, Hope
It can be carried out according to the search process or synthetic route design process method for ITS described in the specifications of No. 60-221087 and Japanese Patent Application No. 60-226581. Double imaginary transition structures and/or bond tables, structural diagrams and/or bond tables of chemical substances represented by ionic or covalent bonds can be registered in a computer by storing them in the computer's main memory. Alternatively, the data may be recorded and saved via a suitable recording medium (magnetic disk, optical disk, magnetic tape, etc.) connected to the computer by wire. In addition, the obtained double imaginary transition structure (and/or bond table), the imaginary transition structure displayed with ionic bonds and/or covalent bonds, and the structural diagram of the chemical substance displayed with ionic bonds and/or covalent bonds are ,
It can be recorded on various recording materials such as plain paper using an appropriate recording device, or displayed on a color cathode ray tube connected to a computer or electronic device. Below, the method for recording and retrieving chemical reaction information of the present invention will be further explained using another chemical reaction example. Chemical reaction example 2 Release reaction of amine from ammonium ion This chemical reaction is as follows: R ₃ NHCl + NaOH → R ₃ N + H ₂ O + NaCl
(Reaction formula 2) It is expressed as follows. The double imaginary transition structure of the reaction can be expressed as follows. By applying the PC module and PI module to DITS2, and further applying the PS module and PP module to each, we obtained the structural formulas of the parent system and product system expressed by covalent bonds and ionic bonds. Chemical reaction example 3 Acid hydrolysis reaction of ester This chemical reaction is CH ₃ COOR + H ₂ O → CH ₃ COOH + ROHHB
(Reaction formula 3) It is expressed as follows. Here, B=Cl, OSO ₂ H,
It can be generalized to OSO ₂ R...etc. The double imaginary transition structure of the reaction can be expressed as follows. By applying a PC module and a PI module to DITS3, an imaginary transition structure represented by covalent and ionic bonds was obtained. Chemical reaction example 4 Alkaline hydrolysis reaction of ester This chemical reaction is CH ₃ COOR + H ₂ O → CH ₃ COOH + ROHAOH
(Reaction formula 4) It is expressed as follows. Here, A=Na. The double imaginary transition structure of the reaction can be expressed as follows. By applying PC and PI modules to DITS4, we obtained an imaginary transition structure represented by covalent and ionic bonds. Note that ITS5 (Example 2) and ITS7 (Example 3) can also be represented by the following incomplete ITS according to the conventional reaction formula that omits the description of the acid or alkali that is the catalyst. Here, ITS11 is incorrect when considered from the reaction mechanism, but complete ITS can be obtained by inserting the following recombination with an acid (or alkali) catalyst. Moreover, the common parts of all these ITSs are expressed as follows. Therefore, for example, for the hydrolysis reaction of esters, complete ITS (ITS5, ITS7) and incomplete ITS
By registering (ITS9 to ITS14) in advance, it is possible to use complete ITS for reaction display and ITS14 for reaction search. Chemical reaction example 5 Methylation reaction of cycloheptanone This chemical reaction is a series of reactions A to C: It is expressed as The double imaginary transition structure of the B-stage reaction can be expressed as follows. Further, Table 3 shows a bonding table corresponding to this double imaginary transition structure. By applying PC and PI modules to DITS5, we obtained an imaginary transition structure represented by covalent and ionic bonds.

【table】

【table】

Chemical reaction example 6 Hydrolysis reaction of carbonamide This chemical reaction is It is expressed as A=Na, K... The double imaginary transition structure of the reaction can be expressed as follows. By applying a PC module and a PI module to DITS6, an imaginary transition structure represented by covalent and ionic bonds was obtained. Chemical reaction example 7 Sulfonamide production reaction This chemical reaction is It is expressed as When base B (B=pyridine, N(C ₂ H ₅ ) ₃ ...) is used as a dehydrochlorination agent,
The double imaginary transition structure of the reaction can be expressed as follows. By applying PC module and PI module to DITS7, we obtained an imaginary transition structure represented by covalent and ionic bonds. In addition, A ⁺ OH ^- (A=Na, K...
), the double imaginary transition structure of the reaction can be expressed as follows. By applying PC and PI modules to DITS8, we obtained an imaginary transition structure represented by covalent and ionic bonds. Next, the reaction in which sulfonyl amide is produced by the reaction of sulfonyl chloride and N ^- is expressed as RSO ₂ Cl + LiN (C ₂ H ₅ ) ₂ → RSO ₂ N (C ₂ H ₅ ) ₂ + LiCl (reaction formula 8). . The double imaginary transition structure of the reaction can be expressed as follows. Consider the following reaction as a preliminary step to this reaction. C ₄ H ₉ Li＋HN(C ₂ H ₅ ) ₂ →C ₄ H ₁₀ ＋LiN(C ₂ H ₅ ) ₂
(Reaction formula 9) It is expressed as follows. The double imaginary transition structure of the reaction can be expressed as follows. By overlapping the obtained DITS9 and DITS10, the double imaginary transition structure shown in Reaction Formula 10 below is obtained. RSO ₂ Cl + HN (C ₂ H ₅ ) ₂ + C ₄ H ₉ Li → RSO ₂ N (C ₂ H ₅ ) ₂ + C ₄ H ₁₀ + LiCl (Reaction formula 10) It is clear that DITS11 is essentially the same as DITS8. Chemical reaction example 8 Substitution reaction This chemical reaction is as follows: C ₁₂ H ₂₅ Br＋KCN→C ₁₂ H ₂₅ CN＋KBr
(Reaction formula 11) The double imaginary transition structure of the reaction can be expressed as follows. By applying a PC module and a PI module to DITS12, an imaginary transition structure represented by covalent and ionic bonds was obtained. Chemical reaction example 9 Enolate ion production reaction This chemical reaction is It is expressed as The double imaginary transition structure of the reaction can be expressed as follows. By applying a PC module and a PI module to DITS13, an imaginary transition structure represented by covalent and ionic bonds was obtained. Considering Reaction Equation 9 as a pre-stage of this reaction,
The following reaction formula 13 is obtained. The double imaginary transition structure of reaction formula 13 is DITS10
Obtained by stacking DITS13. Furthermore, the following Reaction Formula 14 is considered as a pre-reaction step. C ₄ H ₉ Br + 2Li → C ₄ H ₉ Li + LiBr (Reaction formula 14) The double imaginary transition structure of Reaction formula 14 can be expressed as follows. A series of reactions consisting of Reaction Formula 14, Reaction Formula 9, and Reaction Formula 12 is expressed as follows. The double imaginary transition structure of this reaction is DITS15,
Obtained by stacking DITS10 and DITS13 in sequence. Chemical reaction example 10 Alcohol dehydration reaction This chemical reaction is It is expressed as Protonic acid HB (HB=
Cl, OSO ₂ H, OTS...), the double imaginary transition structure of the reaction and the imaginary transition structure expressed by covalent bonds and ionic bonds can be expressed as follows. Here, Ph means a phenyl group. Chemical reaction example 11 Acylation reaction by Friedel-Crafts reaction This chemical reaction is It is expressed as Considering the asilisium ion, the first stage of the reaction can be expressed as follows, and its double imaginary transition structure can be expressed as follows. RCOCl+AlCl ₃ →RCO ⁺ AlCl ₄ ^- (Reaction formula 18) Here, R means an m-nitrophenyl group. Next, the following reaction occurs as a second step. The double imaginary transition structure of the reaction can be expressed as follows. A series of reactions consisting of reaction formula 18 and reaction formula 19 is expressed as below, and its double imaginary transition structure is
Obtained by superimposing DITS18 and DITS19. Note that RCO ⁺ AlCl ₄ ^- is displayed as follows. Chemical reaction example 12 Diazonium salt production reaction The production of diazonium salt of aniline is represented by the following two-step reaction. First stage reaction: _PhNH2 + _NaNO2 +HCl→PhNH-N=O+NaCl+ _H2O (Reaction formula 21) The double imaginary transition structure of the reaction can be expressed as follows. Second stage reaction: PhNH−N=O+HCl→PhN ⁺ ≡NCl ^- +H ₂ O
(Reaction formula 22) The double imaginary transition structure of the reaction can be expressed as follows. In addition, diazonium salts are displayed as follows. The reactions of the first and second stages are summarized as follows: PhNH ₂ +NaNO ₂ +2HCl→PhN ⁺ ≡NCl ⁻ +NaCl+2H ₂ O (reaction formula 23). The double imaginary transition structure of the reaction is DITS21
and DITS22. Next, the reaction via this diazonium salt will be considered. Alternatively, ArNH ₂ +NaNO ₂ +H ₂ SO ₄ →ArOH+N ₂ +NaOSO ₂ OH (Reaction formula 24') Here, Ar means a 2,5-dimethylphenyl group. The double imaginary transition structure for the A-step reaction is obtained by replacing HCl with HOSO ₂ OH in DITS23. The double imaginary transition structure of the B-stage reaction can be expressed as follows. In addition, the DITS of the A-stage reaction and the B-stage reaction are
When DITS24 is superimposed, the following double imaginary transition structure is obtained. It is clear that the γ ring of ITS55 is a fusion of the α ring of ITS51 and the β ring of ITS53. Also,
DITS25 and ITS55 correspond to reaction formula 24. Chemical reaction Example 13 Hydrolysis reaction of nitrile This chemical reaction (Org.Synth.Coll.Vol.2, 588)
teeth, It is expressed as The double imaginary transition structure of the reaction can be expressed as follows. In addition, in DITS26

[Formula] or

Trivial H
Name it. This type of H must be expressed precisely as follows. For example, if you extract a single reaction element and express it completely, it will be expressed as follows. Similarly, in DITS26, the remaining two pairs

[Formula] can also be displayed completely. However, since it would be very complicated to include such a display in DITS26, it was handled as trivial H. Also DITS22, DITS23 and DITS25
The same goes for trivial H, which appeared in . Next, chemical reactions (Org.Synth.Coll.Vol.2,
284):

[Formula] The double imaginary transition structure of the A-stage and B-stage reactions can be expressed as follows. Now, if we disassemble ITS58, it can be expressed as follows. The double imaginary transition structure of the entire reaction process consisting of A and B steps can be obtained by superimposing DITS27 and DITS28. The imaginary transition structure displayed with covalent bonds is shown below. (ITS60) Chemical reaction example 14 Hydrolysis reaction of imine This chemical reaction (Org.Synth.Coll.Vol.2, 49)
teeth, It is expressed as Then, the double imaginary transition structure of the reaction can be expressed as follows. Next, a complex reaction of imine and nitrile hydrolysis (Org.Synth.Coll.Vol.2, 310): CH ₂ = N-CH ₂ CN + C ₂ H ₅ OH + 2HCl + 2H ₂ O → ClH・NH ₂ CH ₂ COOC ₂ H ₅ + _CH2O + _NH4Cl
The imaginary transition structure represented by the covalent bond in (Reaction Formula 28) can be expressed as follows. Chemical reaction example 15 Oxidation reaction with sulfoxide Sulfoxide is expressed as follows. This chemical reaction is It is expressed as Here, TsO-R is displayed as follows. Also, sulfone is displayed as follows. If R=C ₇ H ₁₅ , the double imaginary transition structure of the reaction can be expressed as follows. Chemical reaction example 16 Wittzig reaction This chemical reaction is It is expressed as The double imaginary transition structure of each reaction in stages A to D can be expressed as follows. The double imaginary transition structure of the entire reaction process from A stage to D stage can be obtained by superimposing DITS31, 32, 33 and 34. The imaginary transition structure displayed by covalent bonds obtained by superimposing ITS64, 65, 66, and 67 is shown below.

Claims (1)

[Claims] 1. A step of topologically superimposing the structure of a starting material and the structure of a product in a chemical reaction that produces at least one product from at least one starting material; Between the structure of the product material, there are (1) bonds between nodes that exist in common in the starting material and the product material, (2) bonds between nodes that exist only in the starting material, and (3) bonds that exist only in the product material. A step of obtaining bond information in which bonds between nodes are differentiated, and ionic structure information regarding the substance; Based on the bond information and ionic structure information, including charges representing structural changes of the substance in the chemical reaction. Creating an imaginary transition structure, or a bonding table containing information about each node and charge, a binding partner node or charge that binds to the node and the charge, and the bond between the node and/or the charge; the above imaginary transition structure; or recording and storing the connection table in a recording medium attached to the computer; and from the stored imaginary transition structure or connection table,
Chemical reaction information, including the step of searching for the structure of a starting material, the structure of a product, or a partial structure thereof by searching using the above search conditions for bond information or ion information, or a search condition that combines these information; Recording/search methods. 2. A step of topologically superimposing the structure of a starting material and the structure of a product in a chemical reaction that produces at least one product from at least one starting material; (1) bonds between nodes and/or charges that are present in common in the starting material and product; (2) bonds between nodes and/or charges that are present only in the starting material; and (3) only in the product. A step of creating an imaginary transition structure including charges by distinguishing between nodes and/or bonds existing in the , respectively; A step of recording and storing the above imaginary transition structure in a recording medium attached to a computer; and a step of displaying the imaginary transition structure. By computer processing, an imaginary transition structure expressed as an ionic bond can be obtained by removing only the bonds between charges from the imaginary transition structure, or by removing only the charges and the bonds between nodes and charges, and then removing only the bonds between charges. A method for recording and retrieving chemical reaction information, comprising: obtaining an imaginary transition structure represented by a covalent bond by representing it as a bond between nodes corresponding to the . 3. A step of topologically superimposing the structure of a starting material and the structure of a product in a chemical reaction that produces at least one product from at least one starting material; (1) Bonds between nodes and between nodes and charges that exist in common in the starting material and product, (2) Bonds between nodes and between nodes and charges that exist only in the starting material, and (3) Formation. A process of creating an imaginary transition structure by ionic bond representation that distinguishes bonds between nodes and between nodes and charges that exist only in substances; A process of recording and saving the above imaginary transition structure in a recording medium attached to a computer; Then, by computer processing from the recorded imaginary transition structure, the structure of the starting material expressed as ionic bonds is obtained by deleting the bonds (3) between nodes and between nodes and charges that exist only in the generated material, or Alternatively, a method for recording and retrieving chemical reaction information, comprising: obtaining a structure of the product substance represented by ionic bonds by deleting bonds (2) between nodes and between nodes and charges that exist only in the starting material;