The title compound (NAV) has been synthesized by the acylation reaction of l-valine with acryloyl chloride, in alkaline solution. The X-ray crystal and molecular structure was solved and refined in the P212121 space group and was characterized by an almost coplanar H2CCHC(O)N(H)C system, CCCN, CCCO and (C)CC(O)N(H)C torsion angles being +anti periplanar (+ap) (trans, +172(1)Â°), -syn periplanar (-sp, cys) (-8(1)Â°), and (-ap, trans) (-175(1)Â°). The carboxylic group plane is almost perpendicular to the amide plane (dihedral angle: 83(1)Â°) and the OCC(H)N(H) torsion angle is-sp, cys (-28(1)Â°). The CO bond distance at amide is 1.240(3) Ã , whereas the CO bond distances at carboxylic group are 1.200(3) and 1.303(3) Ã , respectively allowing an easy assignment of protonation site. The molecule has been theoretically analyzed via the methods of density functional theory DFT and semi-empirical quantum mechanics at PM3 level (SEQMPM3) in order to examine the conformational surface at the gas phase and in the presence of solvent molecules. The DFT computations at B3LYP/6-311++G** are the most reliable ones among those performed in this work (SEQMPM3, and B3LYP/6-31G**) as the agreement between computed and XRD bond parameters is excellent. Even the conformations are very reliable and the effect of the solvent was evaluated in a box of water molecules (at SEQMPM3) and through the PCM method at DFT for water, methanol, chloroform and other solvents. Â© 2012 Elsevier B.V. All rights reserved.
|Titolo:||X-ray structure and computational study for N-acryloyl-l-valine, a versatile monomer for preparing smart drug delivery carriers|
CINI, RENZO (Corresponding)
|Appare nelle tipologie:||1.1 Articolo in rivista|