H-Bonding-Induced Repulsion Between Small Groups Toward a Highly Puckered Benzene.

Authors

Chaofeng Zhao, Qi Sun, Ning Ding, Xiaoting Ren, Jinxuan He, Shenghua Li, Siping Pang

Published in

Advanced science (Weinheim, Baden-Wurttemberg, Germany). Pages e78352. Oct 18, 2026. Epub Oct 18, 2026.

Abstract

Benzene ring puckering generally arises from the strong repulsion between bulky substituents, while in this study, we present that benzene ring puckering can be achieved by repulsion between small substituents (nitro and methyl groups) facilitated by hydrogen-bonding attraction, as exemplified in 1,3,5-trinitro-2,4,6-trimethylaminobenzene. The role of intramolecular hydrogen bonding and steric repulsion is further investigated through comparison with four structurally related compounds differing in hydrogen-bond donor availability and substituent size.

PMID:
42893474
Bibliographic data and abstract were imported from PubMed on 19 Oct 2026.

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