A comment on nomenclature and the unsaturated bond

Polton, Donald J.

doi:10.1021/ci00001a013

Cited by 32 publications

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“…18 principal Component. Computer studies have indicated that it is advantageous to deal with degree of substitution and bridging rather than size when selecting the principal component of a structure for nomenclature purposes.…”

Section: Problems With Current Nomenclaturesmentioning

confidence: 99%

“…Finally, the apparently anomalous ordering of the triple bond in most, if not all, nomenclature systems between the single and double bond has been discussed at some length in a recent paper. 18 Principal Component. Computer studies have indicated that it is advantageous to deal with degree of substitution and bridging rather than size when selecting the principal component of a structure for nomenclature purposes.…”

Section: Problems With Current Nomenclaturesmentioning

confidence: 99%

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Systematic chemical nomenclatures in the computer age

Kirby¹,

Polton²

1993

J. Chem. Inf. Comput. Sci.

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This paper draws upon experience in the development of computer software which generates and analyzes systematic organic chemical nomenclatures and highlights some general points where these nomenclatures cause difficulties in computer processing. It is suggested that the tackling of these points would, through consequent simplification, tightening, and improved consistency of the rules, help scientists and students in their use of nomenclature both by manual means and by computer. This might gradually lead to the development of a new systematic nomenclature, formally defined, which could co-exist for some time with current nomenclatures, supported by software to provide interconversion between it and them. INTRODUCTIONOnly quite recently has progress been made, other than for indexing purposes, in computer recognition and translation of general systematic organic chemical nomenclature^.'-^ That it has taken so long to be able to recognize and generate systematic nomenclatures and to interconvert them with structural representations results from the many problems encountered in analyzing and generating nomenclatures by computer. This has led us to consider whether it is time for nomenclature to respond to the needs of computer processing through simplification, consistency, and tightening of the rules. This would have the added benefit that scientists could more readily form, understand, and use systematic nomenclature both with and without computer systems.The principal use of chemical nomenclature is to give a compound a label that can be spoken, written, and used in printed indexes and from which the structure can be perceived by scientists. While trivial nomenclature has the benefit of conciseness, only systematic nomenclature, which to a certain extent gives pronunciation and semantics to a structure, is of use for unambiguously labeling a structure with a name that can safely be communicated worldwide. The compilation by Lees and Smitha of the papers presented at a symposium held in 198 1 to discuss the use and the problems of nomenclature, and to help overcome the confusion and misunderstandings that existed, remains a valuable record of many of the issues. Typical of these is that IUPAC systematic organic nomenclature' has some similarities to a natural language8 in that it has evolved. So it includes some commonly used trivial names, contains redundant information, allows a structure to have more than one name, and requires expertise in applying the rules to determine the name for a given structure.As mechanization was applied to chemical information, stricter linear representations, or notations, of structures were developed. Such notations represent structures in coded form using symbols which consist to a greater or lesser extent of the ordinary characters for the chemical elements accompanied by other alphanumeric and special characters. Examples include the Wiswesser line notation (WLN)9 and the Dyson-IUPAC notational0 These chemical notations were readily adapted to computer use: registration and s...

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Section: Problems With Current Nomenclaturesmentioning

confidence: 99%

Section: Problems With Current Nomenclaturesmentioning

confidence: 99%

Systematic chemical nomenclatures in the computer age

Kirby¹,

Polton²

1993

J. Chem. Inf. Comput. Sci.

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Modeling and Prediction of Electrophoretic Mobilities in Capillary Electrophoresis: Separation of Alkylpyridines

McKillop¹,

Smith²,

Rowe³

et al. 1998

Anal. Chem.

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Novel Chirality Descriptors Derived from Molecular Topology

Gelbukh

Bonchev

Tropsha

2001

J. Chem. Inf. Comput. Sci.

123

121

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Several series of novel chirality descriptors of chemical organic molecules have been introduced. The descriptors have been developed on the basis of conventional topological descriptors of molecular graphs. They include modified molecular connectivity indices, Zagreb group indices, extended connectivity, overall connectivity, and topological charge indices. These modified descriptors make use of an additional term called chirality correction, which is added to the vertex degrees of asymmetric atoms in a molecular graph. Chirality descriptors can be real or complex numbers. Advantages and drawbacks of different series of chirality descriptors are discussed. These descriptors circumvent the inability of conventional topological indices to distinguish chiral or enantiomeric isomers, which so far has been the major drawback of 2D descriptors as compared to true 3D descriptors (e.g., shape, molecular fields) of molecular structure. These novel chirality descriptors have been implemented in a quantitative structure-activity releationship (QSAR) study of a set of ecdysteroids with a high content of chiral and enantiomeric compounds using the k nearest neighbor QSAR method (kNN) recently developed in this laboratory. We show that the results of this study compare favorably with those obtained with the comparative molecular field analysis (CoMFA) applied to the same dataset. The novel chirality descriptors of molecular structure should find their applications in QSAR studies and related investigations of molecular sdatasets.

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A comment on nomenclature and the unsaturated bond

Cited by 32 publications

References 0 publications

Systematic chemical nomenclatures in the computer age

Systematic chemical nomenclatures in the computer age

Modeling and Prediction of Electrophoretic Mobilities in Capillary Electrophoresis: Separation of Alkylpyridines

Novel Chirality Descriptors Derived from Molecular Topology

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