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Long‐range π‐type hydrogen bond in the dimers CH 2 OHF, CH 2 OH 2 O, and CH 2 ONH 3
Author(s) -
Li Ruiyan,
Li Zhiru,
Wu Di,
Hao Xiyun,
Li Rujiao,
Sun Chiachung
Publication year - 2005
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.20507
Subject(s) - chemistry , hydrogen bond , crystallography , hydrogen atom , hydrogen , atom (system on chip) , single bond , bond energy , lone pair , type (biology) , bond length , low barrier hydrogen bond , stereochemistry , molecule , crystal structure , organic chemistry , ecology , computer science , biology , embedded system , alkyl
Using four basis sets, 6‐311G( d,p ), 6‐31+G( d,p ), 6‐311++G(2 d ,2 p ), and 6‐311++G(3 df ,3 pd ), the optimized structures with all real frequencies were obtained at the MP2 level for dimers CH 2 OHF, CH 2 OH 2 O, CH 2 ONH 3 , and CH 2 OCH 4 . The structures of CH 2 OHF, CH 2 OH 2 O, and CH 2 ONH 3 are cycle‐shaped, which result from the larger bend of σ‐type hydrogen bonds. The bend of σ‐type H‐bond O…HY (YF, O, N) is illustrated and interpreted by an attractive interaction of a chemically intuitive π‐type hydrogen bond. The π‐type hydrogen bond is the interaction between one of the acidic H atoms of CH 2 O and lone pair(s) on the F atom in HF, the O atom in H 2 O, or the N atom in NH 3 . By contrast with above the three dimers, for CH 2 OCH 4 , because there is not a π‐type hydrogen‐bond to bend its linear hydrogen bond, the structure of CH 2 OCH 4 is a noncyclic shaped. The interaction energy of hydrogen bonds and the π‐type H‐bond are calculated and discussed at the CCSD(T)/6‐311++G(3 df ,3 pd ) level. © 2005 Wiley Periodicals, Inc. Int J Quantum Chem, 2005