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A combined experimental and theoretical study of benzoxaborole derivatives by Raman and IR spectroscopy, static DFT, and first‐principle molecular dynamics
Author(s) -
Jezierska Aneta,
Panek Jarosław J.,
Żukowska Grażyna Z.,
Sporzyński Andrzej
Publication year - 2010
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1625
Subject(s) - chemistry , intermolecular force , hydrogen bond , anharmonicity , molecular dynamics , computational chemistry , raman spectroscopy , infrared spectroscopy , spectroscopy , density functional theory , molecule , organic chemistry , quantum mechanics , physics
Physicochemical properties of 1,3‐dihydro‐1‐hydroxy‐3‐morpholin‐4‐yl‐2,1‐benzoxaborole ( IIa ) and 1,3‐dihydro‐1‐ hydroxy‐2,1‐benzoxaborole ( IIb ) were investigated using a combination of spectroscopic and computational approaches. The compound IIa belongs to the group represented by the prototypical benzoxaborole IIb , which exhibits receptor activity toward sugars in aqueous solution. Additionally, the IIb can serve as a pattern structure for physicochemical description of benzoxaborole derivatives. The infrared and Raman spectroscopy measurements were performed in solvents and in the solid state. Furthermore, experimental findings served as a reference data source for further computational investigations. DFT calculations in vacuo were used to estimate the binding energy of the dimeric forms, indicating the strength of the intermolecular hydrogen bonds. AIM and ELF theories were applied to give an insight into the electronic structure of the studied compounds. The last part of this study contains Car–Parrinello molecular dynamics investigations in the solid state. Computational results indicated that the key intermolecular feature, the pair of hydrogen bonds, is rather harmonic and the extent of the anharmonicity is temperature dependent as shown by the OH stretching envelope calculations performed for IIa . Inclusion of the quantum effects in the proton motion does not significantly change the qualitative description of the intermolecular H‐bond dynamics of the investigated compound. Copyright © 2010 John Wiley & Sons, Ltd.