6293-83-0Relevant articles and documents
Triclinic and orthorhombic polymorphs of 2-iodo-4-nitroaniline: interplay of hydrogen bonds, nitro...I interactions and aromatic pi-pi-stacking interactions.
McWilliam,Skakle,Low,Wardell,Garden,Pinto,Torres,Glidewell
, p. 942 - 945 (2001)
In the triclinic polymorph of 2-iodo-4-nitroaniline, C(6)H(5)IN(2)O(2), space group P-1, the molecules are linked by paired N-H...O hydrogen bonds into C(8)[R(2)(2)(6)] chains of rings. These chains are linked into sheets by nitro...I interactions, and the sheets are pairwise linked by aromatic pi-pi-stacking interactions. In the orthorhombic polymorph, space group Pbca, the molecules are linked by single N-H...O hydrogen bonds into spiral C(8) chains; the chains are linked by nitro...O interactions into sheets, each of which is linked to its two immediate neighbours by aromatic pi-pi-stacking interactions, so producing a continuous three-dimensional structure.
NCBSI/KI: A Reagent System for Iodination of Aromatics through in Situ Generation of I-Cl
Palav, Amey,Misal, Balu,Chaturbhuj, Ganesh
, p. 12467 - 12474 (2021/08/24)
In situ iodine monochloride (I-Cl) generation followed by iodination of aromatics using NCBSI/KI system has been developed. The NCBSI reagent requires no activation due to longer bond length, lower bond dissociation energy, and higher absolute charge density on nitrogen. The system is adequate for mono- and diiodination of a wide range of moderate to highly activated arenes with good yield and purity. Moreover, the precursor N-(benzenesulfonyl)benzenesulfonamide can be recovered and transformed to NCBSI, making the protocol eco-friendly and cost-effective.
A novel ternary approach to quantitatively assess the reactivity of nitroaniline regioisomers by investigation of rapid iodination kinetics using hydrodynamic voltammetry, reduction propensities from polarography, and binding affinities from molecular docking simulations
Borkar, Vitthal T.
, p. 1193 - 1202 (2021/07/31)
A novel ternary approach to assess the reactivity of nitroaniline regioisomers on a quantitative scaffold has been manifested on the basis of three complementary tenets: kinetics, polarography, and molecular docking. Data from investigation of rapid iodination kinetics of nitroaniline regioisomers by hydrodynamic voltammetry in aqueous medium, reduction propensities of these regioisomers from polarography, and their binding affinities with hypoxanthine-guanine phophoribosyltransferase (HPRT1) from molecular docking simulations lead to inferences regarding their reactivity that agree in entirety. The experimentally determined magnitudes of the specific reaction rates, energies of activation, collision frequencies, entropies of activation from kinetic studies, and reduction propensities of nitroaniline regioisomers from polarograms when complemented with in silico binding energies of these regioisomer ligands with the receptor enzyme, assess their relative reactivities in unison on a quantitative scaffold. This novel ternary approach unambiguously assesses the reactivity of the regioisomers of nitroaniline as 4-nitroaniline?>?2-nitroaniline?>?3-nitroaniline.