Angle distortion model for predicting enediyne activation towards Bergman cyclization: an alternate to the distance theory

Author:

Bhattacharya Prabuddha1,Chakraborty Soham2,Balaji Ashwin3,Basak Amit4ORCID

Affiliation:

1. Department of Chemistry, Mrinalini Datta Mahavidyapith, Kolkata 700 051, India

2. Department of Chemistry, Indian Institute of Technology (Indian School of Mines), Dhanbad 826 004, India

3. Department of Chemistry, Indian Institute of Technology, Kharagpur 721 302, India

4. Division of Chemical Science, Indian Institute of Science Education and Research, Kolkata 741 246, India

Abstract

Structurally similar enediynes showed decrease in interior proximal bond angles (Pa and Pb) with increase in reactivity. Enediynes with average interior proximal angles [(Pa + Pb)/2] less than 166° undergo cyclization under ambient conditions.

Funder

Indian National Science Academy

Publisher

Royal Society of Chemistry (RSC)

Subject

General Chemical Engineering,General Chemistry

Reference78 articles.

1. p-Benzyne. Generation as an intermediate in a thermal isomerization reaction and trapping evidence for the 1,4-benzenediyl structure

2. Reactive 1,4-dehydroaromatics

3. Evidence for the reactive spin state of 1,4-dehydrobenzenes

4. For a comprehensive overview on cycloaromatizaton reactions leading to the formation of diradicals including the relevant discussion on electronic effects, molecular orbital analysis, ionic and zwitterionic pathways, metal catalyzed cycloaromatizations and secondary aromaticity effects, refer to the following book chapter: A.Campbell , P. W.Peterson and I. G.Alabugin , Cycloaromatization reactions , in AROMATICITY Modern Computational Methods and Application , 1st edn, Elsevier , 2021 , pp. 339–375

5. The Enediyne Antibiotics

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