Table 3. QTAIM Parameters of Electron Density at BCP (ρ_BCP) and Total Electron Energy Density at the BCP (H_BCP) and NBO Energies (ΔE_orb) Corresponding to the n_B → σ_AH* Overlaps^a.

	cis conformationsb
	intramolecular HB O–H···O or S–H···O			intermolecular HB O–H···O or N–H···O
compd	ρBCP (au)	HBCP (au)	ΔEorb (kcal/mol)	ρBCP (au)	HBCP (au)	ΔE (kcal/mol)
benzamide				0.032	0.001	19.3
benzoic acid				0.048	–0.005	43.6
salicylamide	0.048	–0.005	26.0	0.031	0.001	16.8
	(0.048)	(−0.005)	(25.9)
2-mercaptobenzamide	0.025	0.002	5.40	0.031	0.001	18.0
	(0.025)	(0.002)	(7.1)
salicylic acid	0.040	–0.002	17.10	0.047	–0.005	32.1
	(0.040)	(−0.002)	(18.8)
thiosalicylic acid	0.031	0.002	10.6	0.046	–0.004	30.7
	(0.031)	(0.002)	(12.9)

	trans conformations
	intramolecular ChBcS···O or O···O			intermolecular HB O–H···O or N–H···O
compd	ρBCP (au)	HBCP (au)	ΔEorb (kcal/mol)	ρBCP (au)	HBCP (au)	ΔE (kcal/mol)
salicylamide	O···O bond path not observed			0.032	0.001	19.2
2-mercaptobenzamide	0.017	0.001	2.0	0.032	0.001	18.6
	(0.016)	(0.001)	(2.3)
salicylic acid	0.015	0.002	0	0.048	–0.005	35.2
	(0.014)	(0.002)	(0)
thiosalicylic acid	0.021	0.001	1.6	0.047	–0.005	39.6
	(0.020)	(0.001)	(4.0)

^aThe results for dimers as well as for monomers (in parentheses) are presented.

^bBenzoic acid and benzamide are not classified as cis or trans conformations since o-substituents do not occur here.

^cChB: chalcogen bond.