Reginato, Marcelo Mota published the artcileConformational study of the electronic interactions and nitric oxide release potential of new S-nitrosothiols esters derivatives of ibuprofen, naproxen and phenyl acids substituted (SNO-ESTERS): Synthesis, infrared spectroscopy analysis and theoretical calculations, Synthetic Route of 73303-88-5, the publication is Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy (2019), 132-142, database is CAplus and MEDLINE.
The conformational study on the new S-nitrosothiols esters (SNO-ESTERS): para-substituted (X = H, OMe, Cl and NO2) S-nitrosothiol derivatives 2-methyl-2-(sulfanyl)propyl phenylacetates (R1), 2-(4-isobutylphenyl)propanoate (ibuprofen, R2), and 2-(4-isobutylphenyl)propanoate of 2-methyl-2-(nitrososulfanyl)propyl (naproxen, R3) was performed using IR spectroscopy (IR) in solvents with increasing polarity (CCl4, CH3Cl, and CH3CN), and theor. calculations, to determine the preferential conformer and the potential of these compounds to release nitric oxide (NO). S-Nitrosothiols were synthesized by esterification reactions, using chlorides of the corresponding carboxylic acids, with good yields (~60%). IR results showed that these compounds presented only one conformation, and the exptl. data were supported by the theor. results obtained by d. functional theory (DFT) calculations using the 6311+G (2df, 2p) basis set. The calculations revealed that all S-nitrosothiols presented one preferential anticlinal (ac) geometric conformation, which agrees with the data obtained exptl. in CCl4. These conformers are stabilized by intramol. hydrogen bonds. Examination of the geometry with regard to the R-SNO group revealed that these compounds are preferentially in the trans (anti) conformation. The calculation of the orbital interactions using the Natural Bond Orbital (NBO) method showed that the nO(NO) → σ*(S-N) hyper-conjugative interaction increases the S-N bond length. The strong nS → π*(NO) interaction and electronic delocalization induces a partial π character to the S-N bond. The weak σS-N bond indicates strong delocalization of the electron pair in O (NO) by the nO(NO) → σ*(S-N) interaction, thereby increasing the capacity of NO release from SNO-ESTERS.
Spectrochimica Acta, Part A: Molecular and Biomolecular Spectroscopy published new progress about 73303-88-5. 73303-88-5 belongs to alcohols-buliding-blocks, auxiliary class Thiol,Aliphatic hydrocarbon chain,Alcohol, name is 2-Methyl-2-sulfanylpropan-1-ol, and the molecular formula is C4H10OS, Synthetic Route of 73303-88-5.
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