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Ionisation of the ZincIodine Bond of Alkylzinc Iodides in Dimethylformamide from Theory and Experiment
Author(s) -
Caggiano Lorenzo,
Jackson Richard F. W.,
Meijer Anthony J. H. M.,
Pickup Barry T.,
Wilkinson Karl A.
Publication year - 2008
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200801313
Subject(s) - electrophile , chemistry , halide , zinc , iodine , reagent , reactivity (psychology) , inorganic chemistry , combinatorial chemistry , organic chemistry , catalysis , medicine , alternative medicine , pathology
Sheep in wolves′ clothing? Quantum chemical calculations suggest that coordination of DMF to alkylzinc iodides can promote ionisation of the zinciodine bond leading to the formation of solvated alkylzinc cations, as depicted. Such cations can also be detected by ESI‐MS measurements. This ionisation may be partly responsible for the compatibility of alkylzinc iodides with acidic protons, as well as the lower reactivity of alkylzinc halides towards electrophiles compared to dialkylzinc reagents.