Rodrigues Silva, Daniela; de Azevedo Santos, Lucas; Hamlin, Trevor A.; Fonseca Guerra, Celia; Freitas, Matheus P.; Bickelhaupt, F. Matthias published their research in ChemPhysChem in 2021. The article was titled 《The Gauche Effect in XCH2CH2X Revisited》.SDS of cas: 624-73-7 The article contains the following contents:
We have quantum chem. investigated the rotational isomerism of 1,2-dihaloethanes XCH2CH2X (X = F, Cl, Br, I) at ZORA-BP86-D3(BJ)/QZ4P. Our Kohn-Sham MO (KS-MO) analyses reveal that hyperconjugative orbital interactions favor the gauche conformation in all cases (X = F-I), not only for X = F as in the current model of this so-called gauche effect. We show that, instead, it is the interplay of hyperconjugation with Pauli repulsion between lone-pair-type orbitals on the halogen substituents that constitutes the causal mechanism for the gauche effect. Thus, only in the case of the relatively small fluorine atoms, steric Pauli repulsion is too weak to overrule the gauche preference of the hyperconjugative orbital interactions. For the larger halogens, X···X steric Pauli repulsion becomes sufficiently destabilizing to shift the energetic preference from gauche to anti, despite the opposite preference of hyperconjugation. The results came from multiple reactions, including the reaction of 1,2-Diiodoethane(cas: 624-73-7SDS of cas: 624-73-7)
1,2-Diiodoethane(cas: 624-73-7) is one of organic iodides. Alkyl iodides react at a faster rate than alkyl fluorides due to the weak C-I bond. Iodo alkanes participate in a variety of organic synthesis reactions, which include the SimmonsSmith reaction (cyclopropanation using iodomethane), Williamson ether synthesis, Wittig reaction, Grignard reaction, alkyl coupling reactions, and Wurtz reaction.SDS of cas: 624-73-7
Referemce:
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com