Halogen bonding in 3-nitrobenzaldehyde derived dichlorodiazadienes

Valentine Nenajdenko, Namiq Shikhaliyev, Abel Maharramov, Gulnar Suleymanova, Gulnara Babayeva, Gunay Mammadova, Irada Shikhaliyeva, Aliyar Babazade, John Arthur Joule
2021 ARKIVOC  
A set of 4,4-dichloro-1,2-diazabutadienes derived from 3-nitrobenzaldehyde was prepared by the copper catalyzed reaction of the corresponding hydrazones with CCl4 in the presence of TMEDA. The structure of all products was confirmed by 1 H and 13 C NMR spectra and ESI-MS. X-ray diffraction revealed Cl···O halogen binding in the crystal form for some dienes. Moreover, Br···π and Cl··π types of halogen bonds are observed. Azo dyes absorb in the UV-Vis region with the max located at about 234−437
more » ... ed at about 234−437 nm in CH2Cl2, DMF and MeOH. Both absorption intensity and max is dependent on the solvent polarity and the electronwithdrawing/donating ability of para-substituents on the aromatic moiety of the dichlorodiazadienes. N N Cl Cl N X Halogen bond Halogen bond acceptor X = CH 3 , Cl, Br 3.075 (CH 3 ) < 3.245 (Cl) < 3.256 (Br) O O d d donor
doi:10.24820/ark.5550190.p011.403 fatcat:67nn3bzoenavhndjatv45ovdyy