5-(4-Chlorophenyl)-1-phenylpyrazolidin-3-one

Liu, Yuan Yuan; Shi, Hong; Chu, Qingyan; Zhu, Hongjun

doi:10.1107/s1600536805041346

Cited by 2 publications

(1 citation statement)

References 6 publications

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“…A survey of the online Cambridge Structural Database (WebCSD), in which H-bond-donor/-acceptor distances were compared, found that the average distance for 2a in five crystals of its derivatives − is 0.147 Å shorter (2.703(2) vs 2.850(4) Å, see Figure a) than for 2a ′ in 12 crystal structures. − Conversely, the average N···N distance in 3a derivatives in three crystal structures − is 0.110 Å longer (3.013(3) vs 2.903(3), see Figure b) than 3a ′ derivatives in five crystal structures. − These observations offer strong experimental support for the notion of aromaticity assisted H-bonding and aromaticity disrupted H-bonding in the cases of 2a and 3a , respectively.…”

Section: Resultsmentioning

confidence: 99%

AMHB: (Anti)aromaticity-Modulated Hydrogen Bonding

Kakeshpour

Jackson

2016

J. Am. Chem. Soc.

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This in silico survey shows that changes in the (anti)aromatic character of π-conjugated heterocycles can be used to fine-tune their hydrogen (H-)bond strengths. Upon H-bonding dimerization, the π-electrons of these rings can be polarized to reinforce or disrupt their (anti)aromatic π-conjugated circuits (πCCs) and stabilize or destabilize the resulting H-bonded complexes. H-bonding interactions that enhance aromaticity or relieve antiaromaticity are fortified, whereas those that intensify antiaromaticity or disrupt aromaticity are weakened, relative to analogues lacking full π-circuits. Computed dissected nucleus-independent chemical shifts, NICS(1)(zz), reveal a uniform pattern and document changes in the magnetic (anti)aromatic character of the heterocycles considered. Recognition of this (anti)aromaticity-modulated H-bonding (AMHB) phenomenon offers insights into a range of fields from organocatalysis and self-assembly to pharmaceutical chemistry and molecular biology.

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