The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Optical rotation and atomic dimension》. Authors are Brauns, D. H..The article about the compound:1-Iodo-2-methylbutanecas:616-14-8,SMILESS:CCC(CI)C).Safety of 1-Iodo-2-methylbutane. Through the article, more information about this compound (cas:616-14-8) is conveyed.
The 1-F, 1-Cl, 1-Br and 1-I derivatives of 2-methylbutane have [M]D20 -799.1°, 179.1°, 610.1° and 1124.7°, resp. If the F derivative is classified with the other halogen derivatives, the values for the ratio Cl-F, Br-Cl and I-Br are 41:18.1:21.6 which agree well with the ratios of the resp. at. diameters.
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Reference:
Thiomorpholine – Wikipedia,
Thiomorpholine | C4H9NS – PubChem