Ethyl esters of coumarin-3-phosphonic acid and 1,2-benzoxaphosphorine-3-carboxylic acid: crystal structure, spectroscopic and theoretical elucidation

Abstract

IR-spectroscopic characterization of the coumarin-3-phosphonic acid and 1,2-benzoxaphosphorine-3-carboxylic acid ethyl esters has been carried out by means of linear-polarized IR (IR-LD) spectroscopy of oriented colloid suspensions in a nematic host. Quantum chemical DFT calculations at the B3LYP level of theory and 6-311??G** basis set were performed. The electronic structure and vibrational properties of both compounds are discussed. The spectroscopic data for 2-benzoxaphosphorine-3-carboxylic acid ethyl ester are in accordance with the crystal structure determined by single crystal X-ray diffraction. The compound C 13 H 15 O 5 P crystallizes in the noncentrosymmetric space group P2 1 2 1 2 1 , and its structure consists of a 3D network formed by short contacts of the type P=OÁÁÁHC (Ar) with distances of 3.420 and 2.467 Å . The geometry of the PO 3 C fragment exhibits a pseudo T d symmetry.

Molecular first order hyperpolarizability and vibrational spectral investigation of Warfarin sodium

“…Their complexation ability in respect to different metal ions has been studied and discussed widely in a considerable number of investigations [5][6][7][8][9]. It has been found that the binding of a metal to the coumarin moiety retains or even enhances its biological activity [10][11][12].…”

Interplay of thermochemistry and Structural Chemistry, the journal (volume 19, 2008) and the discipline

“…Therefore, in the next paper Koleva et al [313] used infrared spectroscopy to characterize the ethyl esters of coumarin-3-phosphonic acid and 2-benzoxaphosphorine-3-carboxylic acid, the latter as its P-oxide. The authors also performed quantum chemical DFT calculations on these species.…”

Crystal Structure and Spectroscopic Properties of (2-oxo-2H-chromen-3-yl)phosphonic Acid Monoethyl Ester Trihydrate

“…1,2 As a part of our systematic study on the synthesis, 3-10 spectroscopic, and structural characterization of novel coumarins, [8][9][10] their salts, and metal complexes [11][12][13][14][15][16][17][18] with potential biological activity, [1][2][3][4][5] we are presenting here the crystal structure and spectroscopic properties of novel (2-oxo-2H-chromen-3-yl)phosphonic acid monoethyl ester trihydrate, shown in Figure 1.…”