Car-Parrinello and path integral molecular dynamics study of the intramolecular hydrogen bonds in the crystals of benzoylacetone and dideuterobenzoylacetone

被引:23
作者
Durlak, Piotr [1 ]
Latajka, Zdzislaw [1 ]
机构
[1] Univ Wroclaw, Fac Chem, PL-50383 Wroclaw, Poland
关键词
TEMPERATURE X-RAY; BETA-DIKETONES; AB-INITIO; VIBRATIONAL ASSIGNMENT; ENOL FORM; CONFORMATIONAL PROPERTIES; NEUTRON-DIFFRACTION; DFT; COVALENT; BEHAVIOR;
D O I
10.1039/c4cp02569e
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
The dynamics of the intramolecular short hydrogen bond in the molecular crystal of benzoylacetone and its deuterated analogue are investigated using ab initio molecular dynamics simulations. A study on intramolecular hydrogen bonding in 1-phenyl-1,3-butadione (I) and 1-deuteroxy-2-deutero-1-phenylbut-1-en-3-one (II) crystals has been carried out at 160 K and 300 K on the CPMD method level and at 300 K on the PIMD method level. The analysis of the two-dimensional free-energy landscape of reaction coordinate delta-parameter and R-O center dot center dot center dot O distances shows that the hydrogen (deuter) between the two oxygen atoms adopts a slightly asymmetrical position in the single potential well. When the nuclear quantum effects are taken into account, very large delocalization of the bridging proton is observed. These studies indicate that hydrogen bonds in the crystal of benzoylacetone have characteristic properties for the type of bonding model resonance-assisted hydrogen bonds (RAHB) without existing the equilibrium of the two tautomers. The infrared spectrum has been calculated, and a comparative vibrational analysis has been performed. The CPMD vibrational results appear to qualitatively agree with the experimental ones.
引用
收藏
页码:23026 / 23037
页数:12
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