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Peer-reviewedCC BYAdvanced science (Weinheim, Baden-Wurttemberg, Germany)

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

  • Chaofeng Zhao1
  • Qi Sun1
  • Ning Ding1
  • Xiaoting Ren2
  • Jinxuan He2
  • Shenghua Li1
  • Siping Pang1
  1. 1School of Materials Science and Engineering, Beijing Institute of Technology, Beijing, China.
  2. 2Department of Synthesis, Hubei Institute of Aerospace Chemical Technology, Xiangyang, China.
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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.

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Cite

BibTeXRIS
BibTeX
@article{zhao2026hbondinginduced,
  title = {{H-Bonding-Induced Repulsion Between Small Groups Toward a Highly Puckered Benzene.}},
  author = {Chaofeng Zhao and Qi Sun and Ning Ding and Xiaoting Ren and Jinxuan He and Shenghua Li and Siping Pang},
  journal = {Advanced science (Weinheim, Baden-Wurttemberg, Germany)},
  year = {2026},
  month = oct,
  doi = {10.1002/advs.78352},
  url = {https://europepmc.org/article/MED/42893474},
  note = {CC BY},
}
RIS
TY  - JOUR
TI  - H-Bonding-Induced Repulsion Between Small Groups Toward a Highly Puckered Benzene.
AU  - Chaofeng Zhao
AU  - Qi Sun
AU  - Ning Ding
AU  - Xiaoting Ren
AU  - Jinxuan He
AU  - Shenghua Li
AU  - Siping Pang
PY  - 2026
DA  - 2026/10/18
JO  - Advanced science (Weinheim, Baden-Wurttemberg, Germany)
DO  - 10.1002/advs.78352
UR  - https://europepmc.org/article/MED/42893474
AB  - 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.
SN  - 2198-3844
ER  -