33670-60-9Relevant academic research and scientific papers
Weak halogen bonding in solid haloanilinium halides probed directly via chlorine-35, bromine-81, and iodine-127 NMR spectroscopy
Attrell, Robert J.,Widdifield, Cory M.,Korobkov, Ilia,Bryce, David L.
experimental part, p. 1641 - 1653 (2012/06/30)
A series of monohaloanilinium halides exhibiting weak halogen bonding (XB) has been prepared and characterized by 35Cl, 81Br, and 127I solid-state nuclear magnetic resonance (SSNMR) spectroscopy in magnetic fields of up to 21.1 T. The quadrupolar and chemical shift (CS) tensor parameters for halide ions (Cl-, Br-, I-) which act as electron density donors in the halogen bonds of these compounds are measured to provide insight into the possible relationship between halogen bonding and NMR observables. The NMR data for certain series of related compounds are strongly indicative of when such compounds pack in the same space group, thus providing practical structural information. Careful interpretation of the NMR data in the context of novel and previously available X-ray crystallographic data, and new gauge-including projector-augmented-wave density functional theory (GIPAW DFT) calculations has revealed several notable trends. When a series of related compounds pack in the same space group, it has been possible to interpret trends in the NMR data in terms of the strength of the halogen bond. For example, in isostructural series, the halide quadrupolar coupling constant was found to increase as the halogen bond weakens. In the case of a series of haloanilinium bromides, the 81Br isotropic chemical shift and CS tensor span both decrease as the bromide-halogen XB is weakened. These trends were reproduced using both GIPAW DFT and cluster-model calculations of the bromide ion magnetic shielding tensor. Such trends are particularly exciting given the well-known role that NMR has played historically in the characterization of hydrogen bonding.
JOINT EFFECT OF STRUCTURE OF REAGENTS AND TEMPERATURE ON REACTIVITY OF AROYL BROMIDE-PRIMARY ARYLAMINE SYSTEMS IN BENZENE. CROSSED CORRELATION
Shpan'ko, I. V.,Goncharov, A. N.,Likhomanenko, E. E.
, p. 522 - 530 (2007/10/02)
The kinetics of the reactions of aroyl bromides with primary arylamines in benzene were studied at 10, 25, 40, and 55 deg C.The effects of factors (temperature, the structure of the aroyl bromides and primary arylamines) varied separately and in pairs and also the joint effect of the three factors on the process rate were assessed quantitatively.The joint effect of the structure of the primary arylamines and the temperature on the reactivity of the system is nonadditive, and the effect of the structure of the aroyl bromides and temperature is additive.The influence of the varied parameters on the nature of the translation states in the reactions is discussed.
Kinetics of Reactions of ω-Bromo-2-acetonaphthone with Pyridine and Substituted Anilines in Various Solvents
Ananthakrishnanadar, P.,Varghesedharumaraj, G.,Subramanian, S. V.
, p. 953 - 956 (2007/10/02)
Rate constants for the reactions of ω-bromo-2-acetonaphthone with aniline and pyridine in various protic and aprotic solvents have been determined at three temperatures.The rates of reaction with pyridine in simple alcohols are less than those with aniline.Values of Hammet ρ-constant have been obtained for the reactions with substituted anilines in a few solvents.Multiple correlation of log k40 deg C for the reaction with aniline in various alcohols employing several solvent parameters is highly successful.
