The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Ordering transitions in symmetrical molecules》. Authors are Westrum, Edgar F. Jr..The article about the compound:Pentaerythrityltetrabromidecas:3229-00-3,SMILESS:BrCC(CBr)(CBr)CBr).SDS of cas: 3229-00-3. Through the article, more information about this compound (cas:3229-00-3) is conveyed.
The 298.15°K. values of the molal heat capacities and thermodynamic functions of C(CH2OH)4, C(CH2F)4, C(CH2Cl)4, C(CH2Br)4, and C(CH2I)4 were studied relative to the nature of the “”pseudo-rotational”” transitions occurring in the general compounds C(CH2X)4. Although little of unusual nature was manifest in the other 4 compounds, a sharp λ transition of considerable magnitude was found at 249.40°K. in C(CH2F)4, with a heat of transition of 3157.5 ± 2.3 cal./mole and a molal entropy of transition of 12.7 cal./degree mole. In “”pseudo-rotational”” transitions the entropy associated with the change occurring in the symmetry features of the structure, both mol. and crystallographic, should be in agreement with the entropy calculated statistically from the change in the number of symmetry features involved in the transition. The total entropy change for the transition in the fluoride may be considered as the sum of the following entropy terms: 3.56 e.u. for the orientational part of the entropy increment occurring in the transition in neopentane; Rln2 for the orientation of the -CC4 tetrahedron in the fluoride; 4Rln2 for the orientations of the -CH2F tetrahedra, and Rln2 for the introduction of the 4 F atoms into the mol. The total entropy was calculated from these terms to be 12.63 e.u., in excellent agreement with the measured value for the transition entropy of 12.66 e.u. occurring in the fluoride.
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Reference:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem