Spectrochemical, ab initio and density functional studies on the conversion of 2-hydroxybenzonitrile (o-cyanophenol) into the oxyanion

Photochemistry of Salicylaldoxime in Solid Argon: An Experimental and Theoretical Study

“…The dehydration of salicylaldoxime may lead to the formation of 2-cyanophenol, which was postulated to be a minor photolysis product in irradiated hexane and aqueous base solution of salicylaldoxime. [19] The comparison of the frequencies characteristic for C with the reported infrared spectra of 2-cyanophenol [30,31] confirms, indeed, formation of the latter molecule in the studied photoreaction. The water and 2-cyanophenol molecules are both proton donors and acceptors, so, being trapped in the same matrix cage after salicylaldoxime is photodissociated, they may form a hydrogen-bonded complex.…”

“…In Table 2 the experimental frequencies identified for product C are compared with the calculated frequencies for the 2-cyanophenol-H 2 O complex and with the reported experimental frequencies for 2-cyanophenol. [30,31] DFT/B3LYP/6-311++G(2d,2p) calculations resulted in a number of stable structures for the 2-cyanophenol-H 2 O complexes. The seven most stable structures of the 2-cyanophenol-H 2 O complex (in three structures the cya- nophenol has the s-cis conformation and in the other four the s-trans one), their corresponding interaction energies, and their calculated vibrational frequencies are presented in the Supporting Information ( Figure S4; Tables S11 and S12).…”

IR spectral and structural studies of 4‐aminobenzenesulfonamide (sulfanilamide)‐d0, ‐d4, and ‐15N, as well as their azanions: Combined DFT B3LYP/experimental approach

“…This rule is also valid for the bond angles (Table IX); it agrees with the data for carbanions, oxyanions, and other azanions (Refs. [10,13,14,19,34] and references therein). …”

“…The charge change values ⌬q i ϭ q i (anion) Ϫ q i (molecule) are usually quite informative in showing the distribution of the new (e.g., carbanionic, azanionic) changes in anions (Refs. [10,11,13,14,19,20,28,29,34] and references therein). According to the present calculations, the new (azanionic) charge of 2a is distributed, as follows: 0.08e Ϫ , 0.23e Ϫ , and 0.12e Ϫ are delocalized over the amino, phenylene, and sulfonyl groups, respectively, and 0.57e Ϫ remain localized at the azanionic center (cf.…”

Adsorption of benzonitrile at the air/water interface studied by sum frequency generation spectroscopy

“…They are important intermediates in production of benzoguanamine, synthetic pesticides, fatty amines and acids, and could be precursors for synthesis of benzyl amine, which can be used as a pharmaceutical intermediate [21][22][23]. As herbicides, benzonitriles are deliberately introduced into the environment.…”