Intermolecular forces and conformational change upon crystallization: The case of phosphorobenzopyrane derivatives

Abstract

Study on the conformational equilibrium of the alanine dipeptide in water solution by using the averaged solvent electrostatic potential from molecular dynamics methodology J. Chem. Phys. 135, 194502 (2011); 10.1063/1.3658857 Vibrational absorption, vibrational circular dichroism, and theoretical studies of methyl lactate self-aggregation and methyl lactate-methanol intermolecular interactionsThe possible conformations of two phosphorobenzopyrane derivatives ͑I and II͒ are investigated with the help of ab initio and density functional theory methods. Special attention is paid to the conformation around the phosphine group. It is demonstrated that while I possesses the same conformations in the gas and crystal phases, II assumes a conformation in a crystal that is not the lowest energy conformer in the isolated molecule. The effect is explained by the difference in the crystal packing of benzopyrane rings for the two compounds. The higher energy conformer of II is favored in a crystal since it avoids creation of strong repulsive interaction between neighboring molecules due to short interatomic distances.

Crystal and Molecular Structures of New Chromone Derivatives as Empirical Evidence of Intramolecular Proton Transfer Reaction; Ab Initio Studies on Intramolecular H-Bonds in Enaminones

“…There is still little known about phosphorohydrazide derivatives of chromone and their potential biological activity; the possible application in cancer chemotherapy makes the knowledge of their molecular structure of great importance. Hence, in continuation of our previous research on this group of compounds, − the crystal structures of ( E )-3-{[(diphenoxyphosphoryl)-2-methylhydrazone]methyleno}-4-hydroxy-2 H -1-benzopyran-2-ne ( 1 ) and 3-{[(diphenoxythio-phosphoryl)hydrazine]methylidene}-3,4-dihydro-2 H -1-benzopyran-2,4-dione ( 2 ) have been determined by X-ray diffraction method and are analyzed here.…”

Bifurcated Hydrogen Bonds in Crystal Structures of New Phosphorochromone Derivatives

“…Hence, in continuation of our previous research, the crystal structures of (E)-3-{[(diethoxythiophosphoryl)-hydrazon]-methyl}-4-hydroxy-2H-1-benzopyran-2-one (1), (E)-3-{[(diethoxythiophosphoryl)-hydrazono]-methyl}-4H-1-benzopyran-4-one (2), and (E)-3-{[(diphenoxythiophosphoryl)-hydrazono]-methyl}-4H-1-benzopyran-4-one (3) have been determined by the X-ray diffraction method. The investigations were undertaken to obtain structural information regarding details of the molecular conformations as well as the weak interactions in the crystal structures.…”

“…[1][2][3][4] Compounds involving their molecule benzopyrane moiety could be classified as analogues of chromone and coumarine, natural biologically active compounds. They are known to exhibit diverse pharmacological properties.…”

“…This paper is a part of our X-ray studies on a group of bezopyrane derivatives substituted with phosphorohydrazide at position 3. − …”

Co-crystal/salt crystal structure disorder of trichloroacetic acid–N-methylurea complex with double system of homo- and heteronuclear O–H···O/N–H···O hydrogen bonds: X-ray investigation, ab initio and DFT studies

“…A change of an urea molecular structure by a simple N-methyl substituent disturbs its intrinsic symmetry and gives rise to obtaining novel co-crystal structures governed by wide range of intermolecular interactions. Molecular structure in the solid state compared with a gas phase one obtained from quantum-chemical methods may be a source of information about these interactions in the crystal space [53,54]. For these reasons a part of this study was focused on theoretical ab initio and density functional theory (DFT) calculations which are combined with X-ray results.…”