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Molecules 2017, 22(6), 896; doi:10.3390/molecules22060896

Genealogy of Conjugated Acyclic Polyenes

Department of Information Sciences, Faculty of Science, Ochanomizu University (Emeritus) Otsuka 2-1-1, Bunkyo-ku, Tokyo 112-8610, Japan
Academic Editor: Shunichi Fukuzumi
Received: 30 April 2017 / Revised: 24 May 2017 / Accepted: 24 May 2017 / Published: 29 May 2017
(This article belongs to the Special Issue Cutting-Edge Organic Chemistry in Japan)
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Abstract

Based on the total π-electron energies Eπs of Hückel Molecular Orbital (HMO) method for all the possible isomers of conjugated acyclic polyenes (C2nH2n+2) up to n = 7, the structure–stability relation of the possible isomers was analyzed. It was shown that the mean length of conjugation L can roughly predict the ordering of stability among isomers, while the Z-index, or Hosoya-index, can almost perfectly reproduce their stability. Further, the genealogy of the conjugated acyclic polyene family was obtained by drawing systematic diagrams connecting these isomers of different n, and governed by several simple rules. Namely, the stability change of a given isomer in the genealogy connecting n and n + 1 polyenes can be classified into three different modes of vinyl addition (elongation, inner and outer branching) and horn growing, i.e., substitution of –HC=CH– moiety with –HC(=CH2)–C(=CH2)H–. By using the Z-index, we can extend this type of discussion to polyene radicals and even to “cross-conjugated” cyclic polyenes containing only one odd-membered cycle, such as radialene and fulvene. View Full-Text
Keywords: total π-electronic energy of HMO; conjugated polyene; topological index; Hosoya index; structure-stability relation; Kekulé structure; mean length of conjugation; cross-conjugation; branching total π-electronic energy of HMO; conjugated polyene; topological index; Hosoya index; structure-stability relation; Kekulé structure; mean length of conjugation; cross-conjugation; branching
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Hosoya, H. Genealogy of Conjugated Acyclic Polyenes. Molecules 2017, 22, 896.

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