In an article, author is Luna, Alberto, once mentioned the application of 35271-74-0, Application In Synthesis of 3-(4-Chlorophenyl)pentanedioic acid, Name is 3-(4-Chlorophenyl)pentanedioic acid, molecular formula is C11H11ClO4, molecular weight is 242.66, MDL number is MFCD00190249, category is isothiazole. Now introduce a scientific discovery about this category.
Cyano substituent effects on enol and enethiol acidity and basicity: The protonation and deprotonation of 3-hydroxy-2-propenenitrile and its thio analogue
The gas-phase basicity and acidity of 3-hydroxy-2-propenenitrile (3-hydroxyacrylonitrile) and its sulfur-containing analogue, 3-mercapto-2-propenenitrile, have been determined by means of high-level G3B3 ab initio calculations and, in the case of the latter compound, compared with the experimental values obtained by means of FT-ICR mass spectrometry techniques, and with previous reported values for the N equivalent to C-CH equivalent to CH-X (X=CH3, NH2, SiH3, PH2) analogues. For both compounds the Z-isomer is the dominant species in the gas-phase. Protonation takes place in both cases at the cyano group. The loss of the proton from the substituent, was found to be systematically much more favorable than the deprotonation at the HC=CH group. 3-Hydroxy-2-propenenitrile is predicted to be a stronger base by ca. 5 kJmol(-1) than its thio analogue, but a weaker acid by 26 U mol(-1). Both compounds are stronger acids than the corresponding unsubstituted vinyl compounds, because cyano substitution stabilizes much more the deprotonated species than the corresponding neutral compound. There is a clear disagreement between our theoretical estimates for both the gas-phase basicity and the gas-phase acidity of 3-mercapto-2-propenenitrile and the corresponding experimental values, which is consistent with its isomerization to yield isothiazole. (C) 2007 Elsevier B.V. All rights reserved.
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Reference:
Isothiazole – Wikipedia,
,Isothiazole – ScienceDirect.com