Theoretical Investigation of In-Plane Hydrogen-Bonded Complexes of Ammonia with Partially Substituted Fluorobenzenes

Systematic investigation of in-plane hydrogen-bonded complexes of ammonia with partially substituted fluorobenzenes has revealed that fluorobenzene, difluorobenzene, and trifluorobenzene favor formation of cyclic complexes with a C−H···N−H···F−C binding motif. On the other hand, tetrafluorobenzene a...

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Bibliographic Details
Published in:The journal of physical chemistry. A, Molecules, spectroscopy, kinetics, environment, & general theory Molecules, spectroscopy, kinetics, environment, & general theory, 2007-04, Vol.111 (14), p.2772-2777
Main Authors: Singh, Prashant Chandra, Ray, Mohana, Patwari, G. Naresh
Format: Article
Language:English
Subjects:
Ammonia - chemistry
Fluorobenzenes - chemistry
Hydrogen Bonding
Models, Chemical
Models, Molecular
Molecular Structure
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Summary:Systematic investigation of in-plane hydrogen-bonded complexes of ammonia with partially substituted fluorobenzenes has revealed that fluorobenzene, difluorobenzene, and trifluorobenzene favor formation of cyclic complexes with a C−H···N−H···F−C binding motif. On the other hand, tetrafluorobenzene and pentafluorobenzene favor formation of linear C−H···N hydrogen-bonded complexes. The complete absence of exclusively linear N−H···F hydrogen-bonded complexes for the entire series indicates that C−F bond in fluorobenzenes is a reluctant hydrogen-bond acceptor. However, fluorine does hydrogen bond when cooperatively stabilized with C−H···N hydrogen bonds for the lower fluoro analogues. The propensity of fluorobenzenes to adapt to the C−H···N−H···F−C binding motif decreases with the progressive fluorination of the benzene ring and disappears completely when benzene ring is substituted with five or more fluorine atoms.
ISSN:1089-5639
1520-5215
DOI:10.1021/jp0690087