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Molecular geometry as a source of chemical information. Part 2—An attempt to estimate the H‐bond strength: the case of p ‐nitrophenol complexes with bases
Author(s) -
Krygowski Tadeusz Marek,
Zachara Joanna Ewa,
Szatylowicz Halina
Publication year - 2005
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.875
Subject(s) - planarity testing , chemistry , bond length , monotonic function , molecular geometry , bond strength , range (aeronautics) , measure (data warehouse) , computational chemistry , molecule , crystallography , geometry , organic chemistry , mathematical analysis , mathematics , materials science , adhesive , layer (electronics) , database , computer science , composite material
B3LYP/6–311+G** optimizations were carried out for p ‐nitrophenol interacting with the flouride with the only constraints for O…F distance in the range 4.0–2.601 Å (for 19 computational data points) with an assumption of planarity of the system and linearity of OH…F. The monotonic dependences of interaction energies on C—O bond lengths led us to propose the C—O bond length as an approximate parameter to measure the H‐bond strength. Experimental geometries showed that the C—O bond length is very sensitive, and also that it is the most variable structural parameter in these complexes. Copyright © 2004 John Wiley & Sons, Ltd.