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. Author manuscript; available in PMC: 2010 May 13.
Published in final edited form as: J Am Chem Soc. 2009 May 13;131(18):6632–6639. doi: 10.1021/ja9004927

Table 2.

C-Cl BDEs (kcal/mol) of mono- and dichlorothiazole, imidazole, and oxazole using G3B3 (bold) and B3LYP (in parentheses).

graphic file with name nihms-111059-t0011.jpg graphic file with name nihms-111059-t0012.jpg graphic file with name nihms-111059-t0013.jpg graphic file with name nihms-111059-t0014.jpg graphic file with name nihms-111059-t0015.jpg graphic file with name nihms-111059-t0016.jpg
C2-Cl C4-Cl C2-Cl C5-Cl C4-Cl C5-Cl
X = S 93.7
(87.4)		 97.8
(90.8)		 98.8
(92.4)		 94.5
(87.4)		 97.9
(90.3)		 93.6
(86.4)		 98.7
(91.8)		 99.7
(90.7)		 100.4
(92.5)
X = NH 99.4
(93.3)		 100.4
(94.3)		 101.3
(95.4)		 99.9
(93.0)		 100.5
(93.9)		 99.1
(92.4)		 101.2
(94.9)		 101.6
(94.0)		 103.0
(95.7)
X = O 100.3
(94.0)		 101.1
(94.3)		 102.3
(95.7)		 -- -- -- -- -- --