Synthesis, structure and toxicity evaluation of ethanolamine nitro/chloronitrobenzoates: a combined experimental and theoretical study

Table 2 Tabulated ΔpKa and hydrogen-bonding geometry (Å, °) for compounds 1–3

ΔpKa	D–H^…A	d(D–H)	d(H^…A)	d(D^…A)	(DHA)	Symmetry transformation for H-acceptor
1
7.58	N(1)–H(2)^…O(2)	0.89	1.86	2.747 (2)	173	x, y, z
	N(1)–H(1)^…O(2)	0.89	2.12	2.815 (2)	135	x + 1, y + 1, z + 1
	N(1)–H(3)^…O(1)	0.89	2.20	2.868 (2)	131	− x, − y + 1, − z + 1
	O(1)–H(1)^…O(3)	0.82	1.87	2.681 (2)	169	− x, − y + 1, − z + 1
2
7.33	N(1)–H(1)^…O(3)	0.89	1.90	2.766 (2)	164	x, y, z
	N(1)–H(2)^…O(1)	0.89	1.96	2.798 (2)	156	− x, − y, − z
	N(1)–H(3)^…O(1W)	0.89	1.98	2.858 (2)	171	− x + 1, − y, − z + 1
	O(1)–H(1)^…O(3)	0.82	1.90	2.716 (2)	172	x − 1, y, z
	O(1W)–H(1)^…O(2)	0.97	1.99	2.857 (2)	149	− x + 2, − y, − z + 1
	O(1W)–H(2)^…O(2)	1.05	1.71	2.754 (2)	175	x, y, z
3 ^a
6.07	N(2)–H(2)^…O(1)	0.96	1.81	2.738	168	x, y, z
	O(5)–H(5)^…O(2)	0.87	1.81	2.683	177	x, y, z
	N(2)–H(2)^…O(5)	0.94	1.88	2.788	162	− x − 1, + y − 1/2, − z + 1/2
	N(2)–H(2)^…O(2)	0.94	1.81	2.757	170	x + 1, y, z

D and A are hydrogen bond donor and acceptor atoms. ΔpKa = pKa (base) − pKa (acid) were calculated using the pKa data from Ref. [38]. All pKa values have been determined in aqueous solutions
^aData of compound 3 [21] are presented here for comparison with compounds 1 and 2

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