Molecular structure of trans-cinnamaldehyde as determined by gas electron diffraction aided by DFT calculations

Abstract

bThe molecular structure of trans-cinnamaldehyde ((E)-3-phenyl-2-propenal) was determined by means of gas electron diffraction. The nozzle temperature was 165 °C. The results of B3LYP calculations with the 6-31G** basis set were used as supporting information. It was found that this molecule has two stable conformers, s-cis and s-trans, which differ in the orientation of the -CH=O group. Their abundances at 165 °C were determined to be 25±19% and 75%, for the s-cis and s-trans, respectively. This conformational composition is consistent with the prediction by the theoretical calculations. limits of error (3σ) referring to the last significant digit; left arrows in the parentheses mean that the differences to the preceding parameters are fixed.

Determination of the Structure and Catalytic Mechanism of Sorghum bicolor Caffeic Acid O-Methyltransferase and the Structural Impact of Three brown midrib12 Mutations

“…11). The energy barrier, which was observed in trans-cinnamaldehyde, results in a significant portion being in the S-cis-configuration (Egawa et al, 2008). The S-cis-form can establish an analogous hydrogen bond with Asn-128, but this nonproductive binding could cause the observed competitive inhibition (Fig.…”

Structure determination of trans-cinnamaldehyde by broadband microwave spectroscopy

“…In a Table 3 Experimentally determined bond lengths of s-trans-transcinnamaldehyde (r s -structure following Kraitchman's approach and the mass dependent r m -structure) compared to values from ab initio calculations (r e -structure, MP2/6-311++G(2d,2p)) and a gas-electron diffraction (GED, r g -structure) study. 10 For comparison, the structural parameters of acrolein 17 a The r (1) m -fit was performed using one additional adjustable parameter: c c = À0.0218 (13). Table 4 Experimentally determined (r s -structure and r m -structure) bond angles of s-trans-trans-cinnamaldehyde compared to values from ab initio calculations (r e -structure, MP2/6-311++G(2d,2p)) and a gas-electron diffraction (GED, r g -structure) study.…”

“…In a Table 3 Experimentally determined bond lengths of s-trans-transcinnamaldehyde (r s -structure following Kraitchman's approach and the mass dependent r m -structure) compared to values from ab initio calculations (r e -structure, MP2/6-311++G(2d,2p)) and a gas-electron diffraction (GED, r g -structure) study. 10 For comparison, the structural parameters of acrolein 17 a The r (1) m -fit was performed using one additional adjustable parameter: c c = À0.0218 (13).…”

“…The obtained structure is compared to a recent gas-electron diffraction (GED) study. 10 Such a comparison is also interesting from a conceptional point of view. Typically, gas-electron diffraction studies are performed at the elevated temperatures necessary to generate sufficient vapour pressure of the respective molecules.…”

Sintesis Sinamil Benzoat Melalui Reaksi Esterifikasi Antara Benzoil Klorida Dan Sinamil Alkohol Hasil Reduksi Sinamaldehida

“…Sinamaldehida merupakan komponen utama minyak kayu manis (Guenther, 1990, p. 1 (Egawa, Matsumoto, Yamamoto, & Takeuchi, 2008). Sinamil alkohol merupakan suatu senyawa organik yang memiliki gugus fungsi -OH dan apabila direaksikan dengan suatu asil halida dengan bantuan piridina melalui reaksi esterifi kasi akan menghasilkan suatu senyawa ester (Fessenden, 1986, p. 87…”