Tirouflet, J. et al. published their research in Bulletin de la Societe Chimique de France in 1958 | CAS: 42137-24-6

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Formula: C5H2N2O2S

The electronic effect of the CN group in the aromatic and thiophene series was written by Tirouflet, J.. And the article was included in Bulletin de la Societe Chimique de France in 1958.Formula: C5H2N2O2S This article mentions the following:

A Hammet σ constant was determined for the CN group of nitrothiophenenitriles by polarographic reduction. Thiophene and POCl3 in HCONMe2 gave 2-thiophenecarboxaldehyde (I), which with HNO3 gave 4-nitro-2-thiophenecarboxaldehyde, and with HNO3 in Ac2O gave the 5-NO2 isomer. Oximation of the aldehyde followed by dehydration gave 2-cyano-4-nitro-thiophene (II) and the 5-NO2 isomer (III), resp. The half-wave potentials of these compounds, determined at pH 3.10, permitted calculation of σ for the CN group of II and III as 0.69 and 1.0, resp., compared with 0.69 and 0.94 for Ac of the corresponding 2-Ac derivatives The difference in half-wave potentials was sufficient (0.14 v.) to allow quant. determination of II and III, particularly by oscillopolarography (the polarograms are illustrated). The product of nitration of 2-cyanothiophene was thus found to contain 42% II and 58% III. Nitration of 2-acetylthiophene and I gave 52% and 75%, resp., of the 4-NO2 derivative A review of previous determinations of σ for the aromatic CN group is also included. In the experiment, the researchers used many compounds, for example, 4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6Formula: C5H2N2O2S).

4-Nitrothiophene-2-carbonitrile (cas: 42137-24-6) belongs to nitriles. The R-C-N bond angle in and nitrile is 180° which give a nitrile functional group a linear shape. Both the carbon and the nitrogen are sp hydridized which leaves them both with two p orbitals which overlap to form the two π bond in the triple bond. Some nitriles are manufactured by heating carboxylic acids with ammonia in the presence of catalysts. This process is used to make nitriles from natural fats and oils, the products being used as softening agents in synthetic rubbers, plastics, and textiles and for making amines.Formula: C5H2N2O2S

Referemce:
Nitrile – Wikipedia,
Nitriles – Chemistry LibreTexts