1. bookVolume 7 (2014): Issue 2 (October 2014)
Journal Details
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Journal
eISSN
1339-3065
First Published
10 Dec 2012
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2 times per year
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English
access type Open Access

Water effect on the bond dissociation energy of O–H and N–H bonds in phenol and aniline: The testing of simple molecular dynamics model

Published Online: 20 Dec 2014
Volume & Issue: Volume 7 (2014) - Issue 2 (October 2014)
Page range: 123 - 128
Journal Details
License
Format
Journal
eISSN
1339-3065
First Published
10 Dec 2012
Publication timeframe
2 times per year
Languages
English
Abstract

A chemical microsolvation model for solution phase bond dissociation enthalpy (BDE) evaluation by means of molecular dynamics is presented. In this simple model, the primary solvent effect on the BDE values was estimated by placing of five water molecules nearby the studied functional groups evenly. Furthermore, the secondary solvent effect was reflected using the conductor like screening model (COSMO). From the quantum-chemical point of view, the molecular dynamics simulations based on the B3LYP functional in rather small basis set were performed. Despite of the constitutional limitations of the proposed model, the obtained O-H and N-H BDE values in phenol (363 kJ mol-1) and aniline (369 kJ mol-1) are in good agreement with the experimental solution phase data.

Keywords

Becke AD (1988) Phys. Rev. A 38: 3098-3100.Search in Google Scholar

Binkley JS, Pople JA, Hehre WJ (1980) J. Am. Chem. Soc. 102: 939-947.Search in Google Scholar

Bizarro MM, Cabral BC, Dos Santos RB, Simons JAM (1999) Pure Appl. Chem. 71: 1249-1256.Search in Google Scholar

Bordwell FG, Zhang XM, Cheng JP (1993) J. Org. Chem. 58: 6410-6414.Search in Google Scholar

Bordwell FG, Zhang XM, Satish AV, Cheng JP (1994) J. Am. Chem. Soc. 116: 6605-6610.Search in Google Scholar

Ervin KM (2001) Chem. Rev. 101: 391-444.Search in Google Scholar

Fu Y, Liu L, Guo QX (2004) J. Phys. Org. Chem. 17: 282-288.Search in Google Scholar

Fukuyo M, Hirotsu K, Higuchi T (1982) Acta Cryst. B 38: 640-643.Search in Google Scholar

Gomes JRB, Ribeiro da Silva MDMC, Ribeiro da Silva MAV (2004) J. Phys. Chem. A 108: 2119-2130.Search in Google Scholar

Guerra M, Amorati R, Pedulli GF (2004) J. Org. Chem. 69: 5460-5467.Search in Google Scholar

Jonsson M, Lind J, Eriksen TE, Merenyi G (1994) J. Am.Chem. Soc. 116: 1423-1427.Search in Google Scholar

Klamt A, Schuurmann G (1993) J. Chem. Soc. Perkin Trans. 2: 799-805.10.1039/P29930000799Search in Google Scholar

Klein E, Lukeš V (2006a) J. Mol. Struct.: THEOCHEM 767: 43-50.10.1016/j.theochem.2006.04.017Search in Google Scholar

Klein E, Lukeš V (2006b) J. Phys. Chem. A 110: 12312-12320.10.1021/jp063468i17078630Search in Google Scholar

Klein E, Lukeš V, Cibulkova Z, Polovkova J (2006) J. Mol.Struct.: THEOCHEM 758: 149-159.10.1016/j.theochem.2005.10.015Search in Google Scholar

Klein E, Rimarčik J, Lukeš V (2009) Acta Chimica Slovaca 2: 37-51.Search in Google Scholar

Lee C, Yang W, Parr RG (1988) Phys. Rev. B 37: 785-789.Search in Google Scholar

Lind J, Shen X, Eriksen TE, Merenyi G (1990) J. Am.Chem. Soc. 112: 479-482.Search in Google Scholar

McFaul PA, Wayner DDM, Ingold KU (1997) J. Org.Chem. 62: 3409-3412.Search in Google Scholar

Neese F (2012) The ORCA program system, Wiley Interdiscip. Rev.: Comput. Mol. Sci. 2: 73-78.Search in Google Scholar

Parker VD (1992) J. Am. Chem. Soc. 114: 7458-7462.Search in Google Scholar

Pratt DA, DiLabio GA, Mulder P, Ingold KU (2004) Acc.Chem. Res. 37: 334-340.Search in Google Scholar

Rassolov VA, Ratner MA, Pople JA, Redfern PC, Curtiss LA (2001) J. Comp. Chem. 22: 976-984.Search in Google Scholar

Rimarčik J, Lukeš V, Klein E, Rottmannova L (2011) Comp. Theor. Chem. 967: 273-283.Search in Google Scholar

Ruscic B, Berkowitz J, Curtiss, LA, Pople, JA (1989) J.Chem. Phys. 91: 114-121.Search in Google Scholar

Vaganek A, Rimarčik J, Ilčin M, Škorňa P, Lukeš V, Klein E (2013) Comp. Theor. Chem. 1014: 60-67.Search in Google Scholar

Zavodnik VE, Beľskii VK, Zorkii PM (1988) J. Struct.Chem. 28: 793-795. Search in Google Scholar

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