Journal of Chemistry

Research Article

NLO and NBO Analysis of Sarcosine-Maleic Acid by Using HF and B3LYP Calculations

Table 3

(a) Selected NBO results showing formation of Lewis and non-Lewis orbitals for sarcosine-maleic acid by using the HF method with 6-31++G(d,p) and 6-31G(d,p) basis sets. (b) Selected NBO results showing formation of Lewis and non-Lewis orbitals for sarcosine-maleic acid by using the B3LYP method with 6-31++G(d,p) and 6-31G(d,p) basis sets.

(a)


			HF/6-31++G(d,p)					HF/6-31G(d,p)
			%	%s	%p	%d	H.O	%	%s	%p	%d	H.O

H₁₀–C₆		H	37.96	99.91	0.09		s	37.62	99.91	0.09		s
H₁₀–C₆		C	62.04	29.37	70.55	0.08	sp^2.40	62.38	28.72	71.20	0.08	sp^2.48

H₉–C₅		H	38.18	99.91	0.09		s	37.82	99.91	0.09		s
H₉–C₅		C	61.82	29.51	70.41	0.08	sp^2.39	62.18	28.84	71.08	0.08	sp^2.46

O₆=C₇	σ	O	65.79	43.45	55.97	0.58	sp^1.29	66.34	44.55	54.93	0.52	sp^1.23
	σ	C	34.21	33.86	65.97	0.17	sp^1.95	33.66	33.61	66.21	0.19	sp^1.97
	π	O	72.82	0.00	99.49	0.51	p	72.27	0.01	99.48	0.51	p
	π	C	27.18	0.00	99.67	0.33	p	27.73	0.01	99.64	0.35	p

C₇–C₆		C	47.74	36.39	63.47	0.14	sp^1.74	47.14	36.74	63.13	0.13	sp^1.72
C₇–C₆		C	52.26	30.53	69.36	0.11	sp^2.27	52.86	31.10	68.78	0.11	sp^2.21

C₇–O₅		C	31.79	29.63	70.14	0.23	sp^2.37	31.46	29.55	70.20	0.25	sp^2.38
C₇–O₅		O	68.21	34.59	65.02	0.40	sp^1.88	68.54	35.37	64.29	0.34	sp^1.82

C₆–C₅	σ	C	50.07	40.16	59.76	0.08	sp^1.49	50.04	40.16	59.76	0.08	sp^1.49
	σ	C	49.93	39.69	60.23	0.08	sp^1.52	49.96	39.71	60.21	0.08	sp^1.52
	π	C	49.98	0.00	99.87	0.13	p	49.96	0.00	99.86	0.14	p
	π	C	50.02	0.00	99.87	0.13	p	50.04	0.01	99.86	0.14	p

C₅–C₄		C	52.39	30.88	69.01	0.11	sp^2.24	52.79	31.45	68.44	0.11	sp^2.18
C₅–C₄		C	47.61	35.44	64.42	0.14	sp^1.82	47.21	35.94	63.92	0.14	sp^1.78

C₄–O₄		C	32.92	31.14	68.53	0.33	sp^2.20	32.22	30.66	68.98	0.36	sp^2.25
C₄–O₄		O	67.08	38.14	61.73	0.14	sp^1.62	67.78	38.65	61.25	0.09	sp^1.58

C₄–O₃	σ	C	33.86	33.37	66.46	0.18	sp^1.99	33.42	33.31	66.49	0.20	sp²
	σ	O	66.14	42.10	57.39	0.52	sp^1.36	66.58	43.53	55.99	0.48	sp^1.29
	π	C	22.45	0.02	99.60	0.38	p	23.91	0.00	99.60	0.40	p
	π	O	77.55	0.03	99.56	0.41	p	76.09	0.00	99.57	0.43	p

O₅–H₁₁		O	79.8	30.76	68.89	0.34	sp^2.24	79.70	30.44	69.25	0.31	sp^2.27
O₅–H₁₁		H	20.11	99.80	0.20		s	20.30	99.79	0.21		s

C₃–H₇		C	61.85	30.76	68.89	0.34	sp^2.24	61.57	25.65	74.25	0.10	sp^2.90
C₃–H₇		H	38.15	99.80	0.20		s	38.43	99.91	0.09		s

C₃–N₁		C	34.74	20.92	78.89	0.19	sp^3.77	34.81	21.68	78.13	0.19	sp^3.60
C₃–N₁		N	65.26	26.54	73.28	0.18	sp^2.76	65.19	26.78	73.06	0.16	sp^2.73

C₂–C₁		C	52.30	25.80	74.07	0.13	sp^2.87	53.17	26.03	73.84	0.13	sp^2.84
C₂–C₁		C	47.70	36.16	63.71	0.14	sp^1.76	46.83	36.68	63.18	0.14	sp^1.72

C₂–H₃		C	61.71	25.54	74.37	0.10	sp^2.91	62.60	24.97	74.94	0.10	sp³
C₂–H₃		H	38.29	99.91	0.09		s	37.40	99.91	0.09		s

C₂–H₂		C	64.01	27.61	72.31	0.08	sp^2.62	62.80	25.91	73.99	0.10	sp^2.86
C₂–H₂		H	35.99	99.90	0.10		s	37.20	99.90	0.10		s

C₂–N₁		C	35.76	21.16	78.65	0.18	sp^3.72	37.82	23.20	76.64	0.16	sp^3.30
C₂–N₁		N	64.24	26.29	73.52	0.19	sp^2.80	62.18	25.99	73.82	0.19	sp^2.84

H₅–N₁		H	18.94	99.85	0.15		s	17.19	99.85	0.15		s
H₅–N₁		N	81.06	25.72	74.14	0.14	sp^2.88	82.81	25.30	74.60	0.10	sp^2.95

C₁–O₂	σ	C	33.80	34.21	65.62	0.17	sp^1.92	33.27	32.86	66.95	0.19	sp^2.04
	σ	O	66.20	43.57	55.85	0.58	sp^1.28	66.73	43.30	56.15	0.55	sp^1.30
	π	C	25.68	0.01	99.60	0.38	p	28.19	1.11	98.53	0.36	p
	π	O	74.32	0.08	99.38	0.54	p	71.81	1.70	97.74	0.56	p

C₁–O₁		C	31.29	29.66	70.11	0.23	sp^2.36	30.99	29.29	70.31	0.41	sp^2.40
C₁–O₁		O	68.71	36.35	63.29	0.36	sp^1.74	69.01	36.91	62.99	0.11	sp^1.71

O₁–H₁		O	77.09	24.41	75.27	0.33	sp^3.08	76.04	24.44	75.46	0.10	sp^3.09
O₁–H₁		H	22.91	99.83	0.17		s	23.96	99.65	0.35		s

(b)


			B3LYP/6-31++G(d,p)					B3LYP/6-31G(d,p)
			%	%s	%p	%d	H.O	%	%s	%p	%d	H.O

H₁₀–C₆		H	37.07	99.95	0.05		s	36.92	99.95	0.05		s
H₁₀–C₆		C	62.93	29.09	70.87	0.04	sp^2.44	63.08	28.37	71.59	0.04	sp^2.52

H₉–C₅		H	37.11	99.95	0.05		s	36.96	99.95	0.05		s
H₉–C₅		C	62.89	29.37	70.59	0.04	sp^2.40	63.04	28.67	71.29	0.04	sp^2.49

O₆=C₇	σ	O	64.92	39.96	59.61	0.43	sp^1.49	65.55	41.16	58.47	0.38	sp^1.42
	σ	C	35.08	33.77	66.13	0.10	sp^1.96	34.45	33.36	66.53	0.11	sp^1.99
	π	O	68.57	0.01	99.66	0.34	p	67.80	0.02	99.65	0.34	p
	π	C	31.43	0.00	99.83	0.17	p	32.20	0.01	99.81	0.18	p

C₇–C₆		C	47.98	36.75	63.19	0.07	sp^1.72	47.34	37.28	62.65	0.07	sp^1.68
C₇–C₆		C	52.02	31.17	68.78	0.05	sp^2.21	52.66	31.83	68.12	0.05	sp^2.14

C₇–O₅		C	32.69	29.37	70.49	0.15	sp^2.40	32.32	29.20	70.55	0.25	sp^2.42
C₇–O₅		O	67.31	32.51	67.23	0.26	sp^2.07	67.68	33.44	66.49	0.07	sp^1.99

C₆–C₅	σ	C	49.75	39.82	60.14	0.04	sp^1.51	49.77	39.81	60.15	0.04	sp^1.51
	σ	C	50.25	39.75	60.21	0.04	sp^1.51	50.23	39.74	60.22	0.04	sp^1.52
	π	C	48.43	0.00	99.94	0.05	p	48.43	0.01	99.93	0.06	p
	π	C	51.57	0.00	99.95	0.05	p	51.57	0.01	99.94	0.05	p

C₅–C₄		C	51.04	30.95	69.00	0.05	sp^2.23	51.56	31.60	68.35	0.05	sp^2.16
C₅–C₄		C	48.96	37.50	62.44	0.06	sp^1.66	48.44	38.04	61.90	0.06	sp^1.63

C₄–O₄		C	32.14	28.62	71.12	0.26	sp^2.48	31.56	28.27	71.48	0.25	sp^2.53
C₄–O₄		O	67.86	32.97	66.97	0.06	sp^2.03	68.44	33.57	66.38	0.06	sp^1.98

C₄–O₃	σ	C	34.92	33.85	66.06	0.09	sp^1.95	34.32	33.63	66.26	0.11	sp^1.97
	σ	O	65.08	39.68	59.91	0.42	sp^1.51	65.68	41.06	58.57	0.37	sp^1.43
	π	C	29.54	0.01	99.81	0.18	p	30.76	0.00	99.81	0.19	p
	π	O	70.46	0.01	99.67	0.32	p	69.24	0.00	99.67	0.33	p

O₅–H₁₁		O	78.67	28.00	71.74	0.26	sp^2.56	78.32	27.49	72.45	0.06	sp^2.64
O₅–H₁₁		H	21.33	99.88	0.12		s	21.68	99.75	0.25		s

O₄–H₄		O	82.53	30.05	69.91	0.04	sp^2.33	81.87	29.39	70.57	0.04	sp^2.40
O₄–H₄		H	17.47	99.73	0.27		s	18.13	99.72	0.28		s

C₃–H₇		C	61.89	25.56	74.38	0.05	sp^2.91	61.68	24.92	75.02	0.06	sp^3.01
C₃–H₇		H	38.11	99.95	0.05		s	38.32	99.95	0.05		s

C₃–N₁		C	37.59	22.57	77.29	0.14	sp^3.42	37.92	23.17	76.70	0.13	sp^3.31
C₃–N₁		N	62.41	29.68	70.28	0.04	sp^2.37	62.08	29.93	70.03	0.04	sp^2.34

C₂–C₁		C	51.17	24.91	75.02	0.06	sp^3.01	52.50	25.53	74.41	0.06	sp^2.91
C₂–C₁		C	48.83	37.84	62.11	0.05	sp^1.64	47.50	38.02	61.92	0.06	sp^1.63

C₂–H₃		C	62.45	25.41	74.54	0.05	sp^2.93	62.72	24.80	75.15	0.05	sp^3.03
C₂–H₃		H	37.55	99.95	0.05		s	37.28	99.95	0.05		s

C₂–H₂		C	64.49	26.69	73.27	0.04	sp^2.75	62.55	25.11	74.83	0.05	sp^2.98
C₂–H₂		H	35.51	99.94	0.06		s	37.45	99.95	0.05		s

C₂–N₁		C	39.10	23.08	76.79	0.12	sp^3.33	40.33	24.65	75.24	0.11	sp^3.05
C₂–N₁		N	60.90	28.84	71.11	0.05	sp^2.47	59.67	28.66	71.29	0.05	sp^2.49

H₅–N₁		H	27.79	99.89	0.11		s	27.28	99.89	0.11		s
H₅–N₁		N	72.21	24.18	75.76	0.05	sp^3.13	72.72	24.46	75.48	0.05	sp^3.09

C₁–O₂	σ	C	34.67	33.87	66.03	0.10	sp^1.95	33.99	32.91	66.98	0.11	sp^2.03
	σ	O	65.33	40.30	59.27	0.43	sp^1.47	66.01	41.09	58.51	0.40	sp^1.42
	π	C	29.68	0.00	99.80	0.20	p	31.49	0.63	99.18	0.19	p
	π	O	70.32	0.00	99.65	0.35	p	68.51	0.94	98.70	0.36	p

C₁–O₁		C	32.04	28.37	71.39	0.24	sp^2.52	31.53	28.36	71.38	0.26	sp^2.52
C₁–O₁		O	67.96	33.41	66.51	0.08	sp^1.99	68.47	34.41	65.52	0.07	sp^1.90

O₁–H₁		O	76.65	22.39	77.53	0.08	sp^3.46	75.40	21.82	78.11	0.07	sp^3.58
O₁–H₁		H	23.35	99.76	0.24		s	24.60	99.78	0.22		s