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Theoretical investigation of in-plane hydrogen-bonded complexes of ammonia with partially substituted fluorobenzenes

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Title Theoretical investigation of in-plane hydrogen-bonded complexes of ammonia with partially substituted fluorobenzenes
 
Creator SINGH, PC
RAY, M
PATWARI, GN
 
Subject center-dot-o
ab-initio
intermolecular interactions
1,2,4,5-tetrafluorobenzene clusters
hexafluorobenzene interaction
infrared-spectroscopy
pi-systems
fluorine
methanol
water
 
Description 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 center dot center dot center dot N-H center dot center dot center dot F-C binding motif. On the other hand, tetrafluorobenzene and pentafluorobenzene favor formation of linear C-H center dot center dot center dot N hydrogen-bonded complexes. The complete absence of exclusively linear N-H center dot center dot center dot 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 center dot center dot center dot N hydrogen bonds for the lower fluoro analogues. The propensity of fluorobenzenes to adapt to the C-H center dot center dot center dot N-H center dot center dot center dot 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.
 
Publisher AMER CHEMICAL SOC
 
Date 2011-07-15T02:18:37Z
2011-12-26T12:49:11Z
2011-12-27T05:34:58Z
2011-07-15T02:18:37Z
2011-12-26T12:49:11Z
2011-12-27T05:34:58Z
2007
 
Type Article
 
Identifier JOURNAL OF PHYSICAL CHEMISTRY A, 111(14), 2772-2777
1089-5639
http://dx.doi.org/10.1021/jp0690087
http://dspace.library.iitb.ac.in/xmlui/handle/10054/4126
http://hdl.handle.net/10054/4126
 
Language en