Literature DB >> 22801355

Is cyclobutadiene really highly destabilized by antiaromaticity?

Judy I-Chia Wu1, Yirong Mo, Francesco Alfredo Evangelista, Paul von Ragué Schleyer.   

Abstract

The high energy of cyclobutadiene (CBD) is not due primarily to "anti-aromaticity," but rather to angle strain, torsional strain, and Pauli repulsion between the parallel CC bonds. Estimations including block-localized wavefunction (BLW) computations conclude that the enormous ring strain (ca. 60 kcal mol(-1)) far exceeds its antiaromatic destabilization (only 16.5 kcal mol(-1)).

Entities:  

Year:  2012        PMID： 22801355     DOI： 10.1039/c2cc33521b

Source DB:  PubMed          Journal:  Chem Commun (Camb)        ISSN： 1359-7345            Impact factor:   6.222


  6 in total

1.  Bicyclic Baird-type aromaticity.

Authors:  Won-Young Cha; Taeyeon Kim; Arindam Ghosh; Zhan Zhang; Xian-Sheng Ke; Rashid Ali; Vincent M Lynch; Jieun Jung; Woojae Kim; Sangsu Lee; Shunichi Fukuzumi; Jung Su Park; Jonathan L Sessler; Tavarekere K Chandrashekar; Dongho Kim
Journal:  Nat Chem       Date:  2017-07-31       Impact factor: 24.427

2.  Minimal Active Space for Diradicals Using Multistate Density Functional Theory.

Authors:  Jingting Han; Ruoqi Zhao; Yujie Guo; Zexing Qu; Jiali Gao
Journal:  Molecules       Date:  2022-05-27       Impact factor: 4.927

3.  On the large σ-hyperconjugation in alkanes and alkenes.

Authors:  Judy I-Chia Wu; Changwei Wang; William Chadwick McKee; Paul von Ragué Schleyer; Wei Wu; Yirong Mo
Journal:  J Mol Model       Date:  2014-06-10       Impact factor: 1.810

4.  Simultaneous Visualization of Covalent and Noncovalent Interactions Using Regions of Density Overlap.

Authors:  Piotr de Silva; Clémence Corminboeuf
Journal:  J Chem Theory Comput       Date:  2014-06-30       Impact factor: 6.006

5.  Geometry, Electronic Structure, and Pseudo Jahn-Teller Effect in Tetrasilacyclobutadiene Analogues.

Authors:  Yang Liu; Ya Wang; Isaac B Bersuker
Journal:  Sci Rep       Date:  2016-03-21       Impact factor: 4.379

6.  Structure-Property Relationships in Unsymmetric Bis(antiaromatics): Who Wins the Battle between Pentalene and Benzocyclobutadiene?†.

Authors:  Péter J Mayer; Ouissam El Bakouri; Tamás Holczbauer; Gergely F Samu; Csaba Janáky; Henrik Ottosson; Gábor London
Journal:  J Org Chem       Date:  2020-03-30       Impact factor: 4.354
  6 in total

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