Structures and properties of the hydrogen-bond complexes: Theoretical studies for the coupling modes of the pyrazole–imidazole system

Sun, Qiao, Li, Zhen, Zeng, Xiaoqing, Ge, Maofa and Wang, Dianxun (2005) Structures and properties of the hydrogen-bond complexes: Theoretical studies for the coupling modes of the pyrazole–imidazole system. Journal of Molecular Structure. Theochem, 724 1-3: 167-172. doi:10.1016/j.theochem.2005.02.049


Author Sun, Qiao
Li, Zhen
Zeng, Xiaoqing
Ge, Maofa
Wang, Dianxun
Title Structures and properties of the hydrogen-bond complexes: Theoretical studies for the coupling modes of the pyrazole–imidazole system
Journal name Journal of Molecular Structure. Theochem   Check publisher's open access policy
ISSN 0166-1280
1872-7999
2210-271X
Publication date 2005-06-06
Sub-type Article (original research)
DOI 10.1016/j.theochem.2005.02.049
Volume 724
Issue 1-3
Start page 167
End page 172
Total pages 6
Place of publication Amsterdam, Netherlands
Publisher Elsevier Scientific
Language eng
Subject 030306 Synthesis of Materials
030302 Nanochemistry and Supramolecular Chemistry
030603 Colloid and Surface Chemistry
030605 Solution Chemistry
030701 Quantum Chemistry
Abstract The calculations at the B3LYP/6-311+G* level have been performed for Pyrazole–Imidazole (Py–Im) system. Eight Py–Im complexes are found and their calculated geometric structures, relative energies, IR spectra and stabilization energies are presented. Those Py–Im complexes can be classified into single H-bond mode and double H-bond mode. The single H-bond complexes can be subdivided into N–Hcdots, three dots, centeredN mode and C–Hcdots, three dots, centeredN mode. The four single H-bond complexes are defined as SA, SB, SC, and SD and the four double H-bond complexes are defined as DA, DB, DC, and DD. SA and SB belong to the N–Hcdots, three dots, centeredN coupling mode while SC and SD belong to the C–Hcdots, three dots, centeredN coupling mode, respectively. The double H-bond coupling mode complexes can be further divided into two types. DA and DB have a N–Hcdots, three dots, centeredN type H-bond and a C–Hcdots, three dots, centeredN type H-bond and DC and DD have two C–Hcdots, three dots, centeredN type H-bonds. For the single H-bond modes and double H-bond modes, the complexes with N–Hcdots, three dots, centeredN type H-bond have stronger interactions than those with C–Hcdots, three dots, centeredN type H-bond. DB is the most stable isomer among the eight complexes. With corrections for the zero-point vibrational energies (ZPE) and basis set superposition errors (BSSE), the stabilization energy of DB is 7.60 kcal/mol at the B3LYP/6-311+G* level. The stability order of the eight Py–Im complexes is DB>DA>SB>SA>SC=SD>DD>DC. Moreover, this result is in close agreement with that of the natural bond orbital (NBO) analysis.
Keyword DFT method
Pyrazole–imidazole complexes
Stabilization energies
NBO analysis
Q-Index Code C1
Q-Index Status Provisional Code
Institutional Status Non-UQ

 
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