Quantum Chemical and Spectroscopic Investigations of (Ethyl 4 hydroxy-3-((E)-(pyren-1-ylimino)methyl)benzoate) by DFT Method

Table 5

Vibrational wavenumbers obtained for the title compound at B3LYP/6-311++G (2d, 2p) (Harmonic frequency (cm⁻¹), IR_int (cm⁻¹)).

Experimental wavenumbers (cm^−1)	Calculated wavenumbers (cm^−1)	IRint (cm^−1)	Raman (cm^−1)	PED	Interpretation
	3224.31	4.48	183.79	s11 93	𝜐𝑠 (CH2), ring 1
	3212.1	9.19	87.51	s13 94	𝜐𝑠 (CH2), ring 4
3200	3205.53	2.7	72.41	s3 94	𝜐as (CH2), ring 1
	3191.45	60.42	530.75	s19 97	𝜐𝑠 (CH3), ring 5
	3189.28	27.8	114.52	s14 92	𝜐𝑠 (CH2), ring 4
	3183.94	1.57	36.38	s4 99	𝜐𝑠 (CH), ring 1
3181	3181.15	51.58	278.89	s18 96	𝜐𝑠 (CH2), ring 3
	3171.65	24.78	229.97	s12 −13 s15 −83	𝜐as (CH2), ring 5 + 𝜐𝑠 (CH), ring 4
	3167.97	2.75	45.05	s12 78 s15 −15	𝜐as (CH2), ring 4 + 𝜐𝑠 (CH2), ring 5
	3167.24	11.88	60.89	s7 92	𝜐as (CH2), ring 2
	3161.69	0.24	47.53	s17 93	𝜐as (CH3), ring 5
	3158.71	1.74	40.37	s16 93	𝜐as (CH2), ring 3
	3119.2	48.59	16.84	s5 −13 s6 −10 s8 −17 s10 60	Not defined
	3099.91	38.21	156.66	s6 −81	𝜐as (C^AH2)
3090	3090.57	0.93	95.26	S8 78 s10 −12	𝜐as (C^AH2)+ 𝜐𝑠 (CH2)
	3059.21	20.49	88.61	s2 99	𝜐𝑠 (C^AH)
	3052.38	15.95	154.12	s9 96	𝜐𝑠 (C^AH2)
	3029.99	26.36	191.4	s5 76 s10 21	𝜐𝑠 (C^AH3)
	2894.86	785.16	225.28	s1 96	𝜐𝑠 (C^AO)
	1675.14	219.1	561.69	s26 −60	𝜐𝑠 (C^AO)
1711	1667.79	12.27	1522.05	s39 42	𝜐𝑠 (C–C), ring 3, 4, 5
	1648.5	371.86	211.55	s20 32 s23 −10	𝜐𝑠 (C^AO) + 𝜐𝑠 (C–C), ring 1, 4
	1643.33	51.26	229.63	s20 −16 s23 −28	𝜐𝑠 (C^AO) + 𝜐𝑠 (C–C), ring 1, 4
	1638.23	39.05	1129.96	s23 −16 s28 −22	𝜐as (C–C), ring 3 + 𝜐as (C–C), ring 4
	1629.61	22.25	3026.04	s21 11 s28 −23	𝜐𝑠 (C–C), ring 1 + 𝜐as (C–C), ring 5
	1622.07	16.12	824.95	s27 13 s81 11	𝜐𝑠 (C–C), ring 4 + 𝛽CCC, ring 5
1610	1610.7	78.32	8784.86	s35 27	𝜐𝑠 (C^AN)
	1583.63	8.54	225.08	s36 21 s39 −10 s60 11	𝜐𝑠 (C–C), ring 2 + 𝜐as (C–C), ring 3 + 𝛽HCC, ring 3
	1554.36	6.42	3.52	s62 70 s101 15	𝛽HCC + 𝜏HCOC, (OC^A)
	1546.99	13.7	1548.31	s33 16 s68 −24	𝜐𝑠 (C–C), ring 3 + 𝛽HCC, ring 2
	1539.54	8.07	29.88	s61 70 s62 −10 s103 10	𝛽HCH,0020(HC^A) + 𝛽HCH, (HC^A) + 𝜏HCOC, (OC^A)
	1526.21	9.1	23.7	s59 73 s100 −12	𝛽HCH, (HC^A) + 𝜏HCOC, (OC^A)
	1524.23	37.79	260.32	s25 12 s72 −10	𝜐𝑠 (C=C), ring 5 + 𝛽HCH, ring 1
	1518.08	71.68	2628.38	s25 11 s55 −14 s56 −10	𝜐𝑠 (C=C), ring 2 + 𝛽HCC, ring 1
	1495.75	21.77	369.81	s67 −25	𝛽HCC, ring 3
	1493.07	89.53	2975.2	s35 −13 s54 17	𝜐𝑠 (C^AN) + 𝛽HOC
	1476.41	4.86	4.47	s60 22	𝛽HOC
	1465.71	3.62	246.14	s71 −65	𝛽HCC, ring 5
	1457.66	12.6	15.74	s63 84	𝛽HCC, (HC^A)
	1451.13	6.85	16.4	s54 −11	𝛽HOC, (OC^A)
	1444.01	6.01	106.44	s29 −15 s69 10	𝜐𝑠 (C–C), ring 5 + 𝛽HCC, ring 3
	1422.52	3.56	1171.11	s22 34	𝜐𝑠 (C=C), ring 2
	1418.96	8.01	160.33	s62 11 s101 67	𝛽HCH, (HC^A) + 𝜏HCOC, (OC^A)
	1407.13	11.57	189.62	s31 −23 s64 −17	𝜐as (C–C), ring 5 + 𝛽HCN, (NC^A)
	1387.02	4.94	692.54	s31 −11 s64 31	𝜐as (C–C), ring 5 + 𝛽HCN, (NC^A)
	1371.3	53.01	744.64	s24 −51 s42 13	𝜐as (C–C), ring 1 + 𝜐𝑠 (C–C), ring 5
	1365.37	3.17	20.73	s85 10	𝛽CCC, ring 4
	1347.53	8.32	30.53	s37 −41 s66 −10	𝜐as (C=C), ring 2 + 𝛽HCC, ring 4
	1322.41	32.6	186.95	s56 −45	𝛽HCC, ring 1
	1301.85	0.32	18.48	s58 76	𝛽HCC, (C^AH)
	1293.46	1.16	19.8	s33 12 s60 10 s68 21	𝜐as (C–C), ring 3 + 𝛽HCC, ring 4 + 𝛽HCC, ring 5
	1290.84	115.58	764.31	s30 58	𝜐𝑠 (CO), (C^AO)
	1284.22	2.96	455.48	s41 20 s69 −17	𝜐𝑠 (C–C), ring 5 + 𝛽HCC, ring 5
	1264.63	151.27	24.03	s26 −16 s57 −14	𝜐as (C–C), ring 5 + 𝛽HCC, ring 1
	1263.15	62.22	3895.41	s41 −11 s44 −11	+ 𝜐as (C–C), ring 1 + 𝜐as (C–C), ring 5
	1252.17	107.36	376.98		Not defined
	1231.74	194.37	485.07	s32 −10 s72 21	𝜐as (C–C), ring 2 + 𝛽HCC, ring 5
	1223.49	154.6	440.05	s70 −52	𝛽HCC, ring 2
	1211.31	266.52	575.9	s70 −13	𝛽HCC, ring 2
	1196.58	52.39	47.76	s25 17 s66 40	𝜐𝑠 (C=C), ring 4 + 𝛽HCC, ring 5
	1190.05	0.98	29.65	s39 14s65 49	𝜐𝑠 (C=C), ring 3 + 𝛽HCC, ring 3
	1188.46	5.77	4.66	s58 −14 s100 54	𝛽HCC (C^AH) + 𝜏HCOC, (OC^A)
	1163.11	62.3	4.06	s29 25s57 55	𝜐𝑠 (C=C), ring 1 + 𝛽HCC, ring 1
	1147.16	3.05	19.94	s48 22 s61 −18 s94 −12 s103 −32	𝛽HCH (C^AH) + 𝛽CCO (C^AO) + 𝜏HCCO (OC^A)
	1143.32	0.51	14.59	s77 32	𝛽CCC, ring 4
	1132.55	18.83	225.65	s69 11	𝛽HCC, ring 5
	1118.58	268.59	4.61	s46 −31 s55 15	𝜐as (C=C), ring 1 + 𝛽HCC, ring 1
	1085.93	16.59	30.98	s27 14 s34 22	𝜐𝑠 (C=C), ring 3 + 𝜐𝑠 (C=C), ring 5
	1039.71	88.12	4.02	s47 72	𝜐as (C=C), (C^AH)
	1037.69	2.7	6.89	s102 −80	𝜏HCCC, ring 4
	1015.71	1	19.59	s112 −52	𝜏HCCC, ring 5
	1014.43	16.39	160.22	s99 −66	𝜏HCNC, (C^AN)
	1005.48	0.18	0.64	s113 61	𝜏HCCC, ring 3
	1004.51	5.05	79.88	s106 74	𝜏HCCC, ring 1
	995.67	6.4	4.17	s32 10 s40 −12	𝜐𝑠 (C–C), ring 2 + 𝜐as (C=C), ring 3
	982.59	1.21	30.45	s109 66	𝜏HCCC, ring 2
	966.87	5.99	189.31	s97 38	𝜏HCCC, ring 1
	964.36	22.39	3.01	s97 44	𝜏HCCC, ring 1
	957.27	80.57	1.93	s96 75	𝜏HOCC (C^AO)
	938.59	1.65	4.09	s110 72	𝜏HCCC, ring 5
	925.25	33.74	166.09	s44 −11 s79 −27	𝜐as (C^AN) + 𝛽CCC, ring 4
	881.43	111.2	18.99	s108 −60	𝜏HCCC, ring 2
	876.59	42.03	10.19	s48 −12 s107 25	𝜐as (C–C), ring 1 + 𝜏HCCC, ring 4
	867.61	38.53	2.37	s98 60	𝜏HCCC, ring 1
	866.7	25.46	2.94	s48 −16 s98 −21 s107 −12 s108 −14	Not defined
	846.41	10.78	2.34	s50 −54	𝛽CCC, ring 4
	833.53	3.4	6.97	s107 14 s111 31	𝜏HCCC, ring 1 + 𝜏HCCC, ring 3
	830.77	0.38	2.5	s104 70	𝜏HCCO, (C^AO)
	828.69	9.21	66.05	s111 21	𝜏HCCC, ring 2
	815.14	3.69	7.4	s128 −18	𝜏CCCC, ring 5
	804.43	1.77	4.67	s73 −27	𝛽OCO, (C^AO)
	793.29	1.08	59.46	s43 20 s82 18	𝜐𝑠 (C–C), ring 1 + 𝛽CCC, ring 4
	778.97	8.82	4.11	s114 67	𝜏HCCC, ring 5
	764.69	5.88	9.65	s82 17	𝛽CCC, ring 1
	760.34	19.23	0.69	s136 −51	𝜙CCCC, ring 1
	741.78	17.23	0.25	s107 −12 s111 11 s116 −11	𝜏HCCC, ring 1 + 𝜏HCCC, ring 4 + 𝜏CCCC, ring 5
	724.92	6.87	6.4	s141 55	𝜙OCOC, (C^AO)
	714.44	0.19	18.14	s28 −11 s49 16	𝜐𝑠 (C–C), ring 3 + 𝛽CCC, ring 4
	702.64	8.92	32.91	s120 −15 s138 −10 s140 −24	𝜏CCCC, ring 1 + 𝜙CCCC, ring 2 + 𝜙CCCC, ring 3
	676.97	30.47	11.99	s41 11 s93 14	𝜐𝑠 (C–C), ring 1 + 𝛽CCO, (C^AO)
	651.45	14.72	11.48	s51 −35	𝛽CCC, ring 1
	640.97	13.61	40.41	s126 12 s129 −11	𝜏CCNC, ring 1 + 𝜏CCCC, ring 1
	622.1	2.3	28.46	s38 −13 s80 17	𝜐𝑠 (C–C), ring 3 + 𝛽CCN, (C^AN)
	578.44	0.11	9.98	s41 10 s49 10	𝜐𝑠 (C–C), ring 3 + 𝛽CCC, ring 5
	568.57	2.75	12.66	s121 −11 s122 −12 s124 −11s139 15	Not defined
	559.84	0.71	13.11	s122 23 s124 10 s134 19	𝜏CCCC, ring 1 + 𝜏CCCC, ring 3 + 𝜙CCCC, ring 5
	546.17	11.74	2.14		Not defined
	537.81	3.67	6.23	s52 24	𝛽CCO, (C^AO)
	530.02	1.06	12.8	s117 24 s139 13	𝜏CCCN, (C^AN) + 𝜙CCCC, ring 3
	521.45	3.05	74.21	s125 22 s127 14	𝜏CCCC, ring 3 + 𝜏CCNC, (C^AN)
	512.46	0.83	1.44	s88 23	𝛽CCC, ring 3
	497.39	3.19	11.62	s76 −14 s83 11 s85 −15	𝛽CCC, ring 3 + 𝛽CCN (C^AN) + 𝛽CCC, ring 5
	483.98	2.27	2.37	s123 −24 s135 24	𝜏CCCC, ring 1 + 𝜙CCCC, ring 2
	460.5	1.9	6.03	s87 20	𝛽CCC, ring 4
	444.53	1.19	3.6	s124 10	𝜏CCCC, ring 1
	432.84	0.68	21.66	s91 41	𝛽CCO (C^AO)
	415.6	2.46	89.07	s22 −11 s90 −14	𝜐as (C–C), ring 4 + 𝛽CCC, ring 3
	386.89	0.5	1.35	s86 −10	𝛽CCC, ring 2
	372.32	11.47	1.34	s75 −16s94 56	𝛽COC, (C^AO) + 𝛽CCO, (C^AO)
	355.13	1.38	4.26	s123 19 s135 10	𝜏CCCC, ring 3 + 𝜙CCCC, ring 5
	346.91	3.4	73.7	s115 −11	𝜏NCCC, (C^AN)
	311.17	4.64	20.43	s45 −15 s95 31	𝜐as (C–C), ring 4 + 𝛽COC, (C^AO)
	289.37	5.1	68.61	s115 24	𝜏NCCC, (C^AN)
	273	0.46	2.42	s105 −10 s121 17 s139 15	𝜏CCCO, (C^AO) + 𝜏CCCC, ring 3 + 𝜙CCCC, ring 5
	267.89	0.58	7.14	s75 13	𝛽COC, (C^AO)
	252.25	1.23	10.57	s103 12s105 55	𝜏CCCO, (C^AO)
	241.04	2.81	9.87	s75 12	𝛽COC, (C^AO)
	223.33	8.26	10.27	s138 −43	𝜙CCCC, ring 4
	186.81	5.98	7.28	s89 12s116 −17	𝛽CCC, (C^A) + 𝜏CCCN, (C^AN)
	171.6	0.34	10.17		Not defined
	152.06	7.4	9.77	s118 24 s133 37	𝜏CCCC, ring 1 + 𝜙COCC, (C^AO)
	134.24	3.04	26.07	s75 −10	𝛽COC (C^AO)
	122.64	0.08	11.46	s119 15 s129 −11	𝜏CCCN, (C^AN) + 𝜏CCNC, (C^AN)
	100.65	1.28	6.44	s119 10 s127 14	𝜏CCCN, (C^AN) + 𝜏CCNC, (C^AN)
	92.61	0.67	7.41	s118 11 s131 −15 s133 −20 s134 13	𝜏COCC, (C^AO)
	79.9	0.64	3.96	s92 23 s131 12	𝛽CCC, ring 4 + 𝜏COCC, (C^AO)
	59.62	0.88	2.9	s130 −16 s131 −37	𝜏COCC, (C^AO)
	39.59	0.12	2.58	s130 48 s131 13 s132 −11	𝜏COCC, (C^AO)
	31.93	0.14	5.25	s74 −42	𝛽CNC (C^AN)
	21.6	0.27	6.59	s126 12 s132 47	𝜏CCNC, (C^AN) + 𝜏COCC, (C^AO)
	16.34	0.3	8.44	s126 18 s132 −22 s135 12	𝜏CCNC, (C^AN) + 𝜏COCC, (C^AO) + 𝜙CCCC, ring 3

𝜐, 𝛽, 𝜏, and 𝜙 denote the stretching, bending, torsion, and out (𝜙 ABCD means the angle between the AD vector and the BCD plane) modes. Indices notation: s: symmetric; as: asymmetric; A: aliphatic; ring 1: C1-C2-C3-C4-C5-C6; ring 2: C15-C16-C17-C18-C19-C20; ring 3: C21-C22-C23-C24-C16-C17; ring 4: C17-C18-C24-C25-C26-C27; ring 5: C23-C24-C25-C28-C29-C30.