Abstract
B3lyp/6–311++g** and mp2/6–311++g** calculations were used to analyze the interaction between CH3SO and HOCl. Nine (complex A: S1A–S9A) and five (complex B: S4B–S7B and S10B) minima were localized on the potential energy surface of CH3SO⋯HOCl complexes at b3lyp/6–311++g** and mp2/6–311++g** computational levels, respectively. The AIM and NBO theories were also applied to explain the nature of the complexes. Bonding energy of complexes A and B corrected with BSSE falls in the ranges of −0.4–−41.4 kJ·mol−1 and −6.9–−35.8 kJ·mol−1 at mp2/6–311++g** level, respectively. The results show that a novel oxygen bond complex (S6) exists in the system, besides hydrogen bond and chlorine bond. Especially, S6B−F, S6B−Br and S7B are blue shifted complexes compared with red shifted S6A, because the electron transfer occurs between LP1(S8) and σ*(O5-Cl7), resulting in the increase of O5-Cl7 and the decrease of vibrational frequency. The complex of S10B has characteristics of both red shift and blue shift.
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References
Hobza P, Sponer J. Structure, energetics, and dynamics of the nucleic acid base pairs: nonempirical ab initio calculations. Chem Rev, 1999, 99: 3247–3276
Li Y B, Zeng Q D, Wang Z H, et al. Constructing supramolecular nanostructure by hydrogen-bonding. Chinese Sci Bull, 2008, 53: 1613–1616
Aloisia S, Franscisco J S. Radical-water complexes in earth’s atmosphere. Acc Chem Res, 2000, 33: 825–830
Grabowski S J. High-level ab initio calculations of dihydrogen-bonded complexes. J Phys Chem A, 2000, 104: 5551–5557
Kollman P A, Liebman J F, Allen L C. Lithium bond. J Am Chem Soc, 1970, 92: 1142–1150
Vila A, Vila E, Mosquera R A. Topological characterization of intermolecular lithium bonding. Chem Phys, 2006, 326: 401–408
Ma J C, Dougherty D A. The cation-π interaction. Chem Rev, 1997, 97: 1303–1324
Cheng J G, Zhu W L, Wang Y L, et al. The open-close mechanism of M2 channel protein in influenza A virus: A computational study on the hydrogen bonds and cation-p interactions among His37 and Trp41. Sci China Ser B-Chem, 2008, 51: 768–775
Dumas J M, Gomel M, Guerin M. Molecular Interactions Involving Organic Halides. New York: John Wiley & Sons Ltd, 1983. 985–1020
Leu M T. Laboratory studies of sticking coefficients and heterogeneous reactions important in the antarctic stratosphere. Geophys Res Lett, 1988, 15: 17–20
Solimannejad M, Alkorta I, Elguero J. Stabilities and properties of O3-HOCl complexes: A computational study. Chem Phys Lett, 2007, 449: 23–27
Zhou Y F, Liu C B T. Theoretical study of HOCl adsorption on ice surface. J Phys Chem Sol, 1999, 60: 2001–2004
Turnipseed A A, Ravishankara A R, Dimethylsulfide: Oceans, atmosphere and climate. In: Restelli G., Ed. Proceeding of the International Symposium Held in Belgirate, Italy, 13–15 October, 1993. New York: Kluwer Academic, 1992. 185
Ravishankara A R, Rudich Y, Talukdar T, et al. Oxidation of atmospheric reduced sulphur compounds: Perspective from laboratory studies. Philos Trans R Soc London Ser B, 1997, 352: 171–182
Li X Y, Fan H M, Meng L P, et al. Theoretical investigation on stability and isomerizations of CH3SO isomers. J Phys Chem, 2007, 111: 2343–2350
Boys S F, Bernardi F. Calculation of small molecular interactions by differences of separate total energies. Some procedures with reduced errors. Mol Phy, 1970, 19: 553–556
Wu D, Li Z R, Hao X Y. An ab initio theoretical prediction: An antiaromatic ring π-dihydrogen bond accompanied by two secondary interactions in a “wheel with a pair of pedals” shaped complex FH⋯C4H4⋯HF. J Chem Phys, 2004, 120: 1330–1335
NIST Standard Reference Database No. 69, March 2003 ed. http://webbook.nist.gov/chemistry, 2005
Alabugin I V, Manoharan M, Peabody S, et al. Electronic basis of improper hydrogen bonding: A subtle balance of hyperconjugation and rehybridization. J Am Chem Soc, 2003, 125: 5973–5987
Wlendening E D, Weinhold F. Natural resonance theory: I. general formalism. J Comp Chem, 1998, 19: 593–609
Bader R F W. Atom in Molecules-A Quantum Theory. Oxford: Oxford University Press, 1990
Bader R F W. A quantum theory of molecular structure and its applications. Chem Rev, 1991, 91: 893–928
Popelier P L A. Characterization of a dihydrogen bond on the basis of the electron density. J Phys Chem A, 1998, 102: 1873–1878
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Supported by the Foundation of Education Committee of Gansu Province (Grant No. 0708-11) and “QingLan” Talent Engineering Funds of Tianshui Normal University
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Li, Z., Li, H., Liu, Y. et al. Weak interaction between CH3SO and HOCl: Hydrogen bond, chlorine bond and oxygen bond. Chin. Sci. Bull. 54, 3014–3022 (2009). https://doi.org/10.1007/s11434-009-0477-8
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DOI: https://doi.org/10.1007/s11434-009-0477-8