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A supramolecular assembly containing an unusually short n‐h…n hydrogen bond ‐ an x‐ray and neutron diffraction study
Author(s) -
Bishop Michael M.,
Lindoy Leonard F.,
Bishop Michael M.,
ThornSeshold Oliver T.,
Piltz Ross O.,
Turner Peter
Publication year - 2001
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570380620
Subject(s) - phthalimide , chemistry , crystallography , supramolecular chemistry , hydrogen bond , neutron diffraction , crystal structure , molecule , stacking , supramolecular assembly , organic chemistry
A supramolecular assembly formed between phthalimide and 2‐guanidinobenzimidazole, containing a short 2.692(4)AR N‐H…N hydrogen bond, is reported. The crystal structure of this species was determined by both X‐ray and neutron diffraction. The diffraction data reveal that the proton involved in the short hydrogen bond has been transferred from the phthalimide to the guanidinobenzimidazole to form an ion pair. There is also an interesting stacking interaction between the atoms involved in the short hydrogen bond and the π system of a phthalimide molecule that is approximately 3.3 Å away. The structure is compared with the structure of a similar assembly formed between 4‐nitrophthalimide and 2‐guanidinobenzimidazole.