Synthesis, spectroscopic, dielectric, molecular docking and DFT studies of (3E)-3-(4-methylbenzylidene)-3,4-dihydro-2H-chromen-2-one: an anticancer agent

Beena, T.; Sudha, L.; Nataraj, A.; Balachandran, V.; Kannan, D.; Ponnuswamy, M. N.

doi:10.1186/s13065-016-0230-8

Table 2 The observed FT-IR, FT-Raman and calculated frequencies (in cm⁻¹) using B3LYP/6-31 + G (d,p) along with their relative intensities, probable assignments, reduced mass and force constants of (3E)-3-(4-methylbenzylidene)-3,4-dihydro-2H-chromen-2-one

From: Synthesis, spectroscopic, dielectric, molecular docking and DFT studies of (3E)-3-(4-methylbenzylidene)-3,4-dihydro-2H-chromen-2-one: an anticancer agent

Mode nos	Observed frequencies (cm⁻¹)		Calculated frequencies (cm⁻¹)		Reduced mass (amu)	Force constant (mdyn/Å)	IR intensity (km/mol)	Raman intensity (Å⁴ amu⁻¹)	Vibrational assignments (PED%)
Mode nos	FTIR	FT Raman	Unscaled	Scaled	Reduced mass (amu)	Force constant (mdyn/Å)	IR intensity (km/mol)	Raman intensity (Å⁴ amu⁻¹)	Vibrational assignments (PED%)
1			23	20	4.139	0.001	0.140	98.862	τ Ring (56), τ CH₃ (20)
2		30	36	29	1.041	0.001	0.259	2.839	τ Ring (56), τ CH₃ (20)
3		43	48	42	4.317	0.006	0.138	4.698	τ Ring (55), τ CH₃ (18)
4		60	61	60	4.037	0.009	0.126	4.758	τ Ring (56), τ CH₃ (20)
5			81	78	6.433	0.025	1.029	1.382	τ Ring (55), τ CH₃ (22)
6			101	96	4.785	0.029	0.456	0.906	γ C=O (58), τ CH₃ (21)
7			156	143	4.419	0.064	1.546	0.321	τ CH₃ (56)
8			189	181	3.393	0.072	0.402	1.098	τ CH₂ (56), γ CH₃ (18)
9		200	225	202	6.604	0.197	2.382	0.235	γ C–CH₃ (54), γ CH (18), γ CH₃ (12)
10			252	237	4.366	0.164	1.529	0.314	γ CC (62), γ CH (20), γ CH₂ (10)
11			274	255	4.050	0.179	1.403	0.314	γ CCC (60), γ CH (22), γ CH₃ (11)
12			314	286	4.114	0.240	0.632	0.065	γ CCC (59), γ CH (18), γ CH₃ (10)
13			327	309	5.288	0.335	1.339	0.029	γ CCC (58), γ CH (18), γ CH₃ (11)
14		350	368	354	3.122	0.249	0.038	0.119	γ CCC (60), γ CH (22), γ CH₃ (12)
15		400	409	400	3.550	0.350	1.104	0.482	γ CCC (62), γ CH (18), γ CH₃ (10)
16			421	413	2.977	0.310	1.829	0.326	γ CCC (62), γ CH (20), γ CH₃ (10)
17			444	437	4.136	0.482	3.120	0.773	γ CCC (62), γ CH (20), γ CH₃ (11)
18		450	457	453	4.033	0.496	3.817	0.144	γ CCC (63), γ CH (18), γ CH₃ (12)
19			490	479	5.515	0.783	24.603	0.378	βC=O (58), βCC (22), βCO (10)
20		500	524	506	2.790	0.452	12.486	0.794	γ C–O (64), γ CH₃ (23), γ CO (10)
21			540	527	5.569	0.786	5.539	0.239	γ CH (58), γ CH₃ (22), γ CC (10)
22		540	545	540	3.662	0.642	4.599	0.033	γ CH (58), γ CC (21), γ CH₂ (11)
23		575	582	572	6.588	1.319	2.309	0.138	γ CH (58), γ CH₃ (20), γ CC (11)
24		600	639	601	6.329	1.526	7.519	0.104	γ CH (56), γ CC (20), γ CH₃ (10)
25			650	633	6.834	1.703	0.662	0.176	γ CH (58), γ CC (18), γ CH₂ (11)
26			693	669	5.112	1.447	4.947	0.007	γ CH (56), γ CH₃ (18), γ CC (12)
27			711	689	3.832	1.142	0.262	0.116	γ CH (56), γ CC (16)
28			727	716	3.876	1.208	9.921	0.085	γ CH (56), γ CC (18)
29		725	737	723	5.549	1.776	11.299	0.128	γ CH (58), γ CC (18)
30			740	735	4.346	1.404	0.599	0.184	βC–CH₃ (60), βCH (23)
31	750		768	748	1.335	0.465	62.541	0.034	βC–O (62), βCC (22)
32			778	760	4.144	1.481	7.458	0.587	βCC (58), βCH (21), βCH₃ (10)
33	810		829	811	1.610	0.653	37.872	0.230	βCCC (63), βCH (21), βCH₃ (12)
34			851	824	1.26	0.540	0.813	0.119	βCCC (63), βCH (18), βCH₃ (11)
35			858	830	3.739	1.625	14.149	0.099	βCCC (62), βCH₃ (20), βCH (10)
36			862	838	2.202	0.964	0.532	0.221	βCCC (62), βCH₃ (21), βCH (12)
37		850	876	850	1.962	0.888	3.587	0.199	βCCC (56), βCH (18), βCH₃ (10)
38			919	861	6.652	3.314	11.953	0.057	βCCC (58), βCH₃ (18), βCH (12)
39			947	869	1.572	0.831	5.009	0.061	βCCC (56), βCH (16), βCH₃ (11)
40		875	954	872	1.399	0.751	11.534	1.087	βCCC (61), βCH (20), βCH₃ (10)
41			970	889	1.579	0.877	5.474	0.037	βCH (78), ν CC (18)
42		900	981	903	1.476	0.837	5.323	0.410	βCH (76), ν CC (16)
43			984	923	1.377	0.786	2.738	0.150	βCH (78), ν CC (13)
44			988	951	1.282	0.738	0.051	0.002	βCH (66), ν CC (16)
45			1010	968	1.409	0.848	2.809	0.020	βCH (66), ν CC (20)
46		990	1033	992	2.848	1.794	2.530	0.024	βCH (70), ν CC (18)
47			1056	1011	2.122	1.396	3.275	0.289	βCH (76), ν CC (18)
48			1060	1029	1.545	1.024	11.399	0.009	βCH (78), ν CC (17)
49			1088	1042	4.259	2.975	171.99	0.044	βCH (78), ν CC (17)
50		1000	1133	1053	1.775	1.344	19.980	0.028	βCH₂ipr (67), βCH (20)
51			1148	1061	1.367	1.063	20.088	0.106	γ CH₂opr (66), βCH (21)
52		1075	1180	1072	1.113	0.914	4.889	0.005	βCH₃ipr (65), βCC (30)
53		1100	1190	1104	2.389	1.994	564.050	3.029	γ CH₃opr (71), βCC (23)
54		1150	1215	1153	1.274	1.109	16.185	0.942	ν CO (58), βCH (18), ν CC (11)
55	1189		1218	1190	1.580	1.381	27.443	0.044	ν CO (58), βCH (18), ν CC (12)
56			1227	1197	2.167	1.924	37.004	1.290	ν C=C (82), βCH₃ (14)
57			1238	1209	2.485	2.247	7.534	0.045	ν CC (71), βCH (16), ν CH₃ (12)
58			1255	1217	2.115	1.964	33.951	0.281	ν C–CH₃ (50), βCH (20), βCO (12)
59	1215		1258	1231	3.099	2.893	219.799	0.644	βCH₂sb (66), βCC (22), βCH (11)
60			1288	1243	1.825	1.785	19.982	0.588	βCH₂asb (70), βCC (20), βCH (10)
61		1250	1340	1250	5.462	5.782	49.937	0.759	βCH₃sb (71), βCC (23), βCH (11)
62	1261		1342	1260	1.625	1.727	2.543	0.527	βCH₃asb (66), βCH (17), ν CC (10)
63			1349	1287	2.373	2.544	13.033	0.436	βCH₃asb (60), βCH (18), ν CC (10)
64			1369	1306	2.450	2.709	31.517	0.047	ν CC (68), βCH (18)
65			1407	1330	1.776	2.074	9.480	0.143	ν CC (66), βCH (19)
66			1420	1343	1.248	1.483	0.324	0.393	ν CC (66), βCH (18)
67			1440	1362	2.310	2.850	7.463	0.084	ν CC (68), βCH (19)
68			1476	1387	1.277	1.449	12.963	0.069	ν CC (68), βCH (19)
69			1491	1395	1.072	1.450	11.786	0.102	ν CC (70), βCH (18)
70			1492	1404	2.295	3.013	30.676	0.013	ν CC (70), βCH (17)
71	1432		1496	1430	1.114	1.469	9.704	0.119	ν CC (68), βCH (17)
72			1529	1487	2.593	3.574	57.049	0.019	ν CC (66), βCH (18)
73	1500		1548	1502	2.482	3.505	23.043	0.262	ν CC (65), βCH (18)
74		1540	1603	1543	5.415	8.200	5.106	0.867	ν CC (66), βCH (19)
75			1636	1587	6.310	9.958	21.097	0.660	ν CC (65), βCH (18)
76			1654	1592	6.049	9.754	145.323	3.229	ν CC (66), βCH (18)
77			1659	1604	6.840	11.109	9.718	0.093	ν CC (68), βCH (18)
78		1600	1668	1615	7.222	11.846	91.204	0.131	ν CC (70), βCH (16)
79	1616	1690	1793	1692	12.541	23.775	370.738	0.460	ν C=O (72), ν CC (14)
80			2980	2801	1.072	5.615	14.012	0.299	ν ssCH₂ (80)
81		2800	3034	2809	1.039	5.641	33.955	0.722	ν assCH₂ (82)
82			3080	2863	1.088	6.085	4.273	0.081	ν ssCH₃ (72), ν CH (23)
83			3092	2889	1.097	6.182	17.402	0.180	ν assCH₃ (80), ν CH (16)
84			3122	2911	1.102	6.330	15.019	0.127	ν assCH₃ (88), ν CH (11)
85			3172	2936	1.088	6.451	3.815	0.088	ν CH (96)
86			3175	2945	1.088	6.464	5.999	0.065	ν CH (96)
87			3177	2962	1.088	6.464	7012	0.109	ν CH (96)
88			3179	2989	1.089	6.488	17.412	0.127	ν CH (98)
89			3192	2993	1.089	6.536	7.580	0.129	ν CH (98)
90			3193	2999	1.094	6.574	14.859	0.219	ν CH (96)
91			3206	3007	1.094	6.629	18.471	0.243	ν CH (98)
92		3020	3218	3018	1.096	6.687	5.949	0.335	ν CH (98)
93		3100	3225	3101	1.091	6.690	6.782	0.076	ν CH (98)

ν, stretching; β, in plane bending; γ, out of plane bending; ω, wagging; τ, torsion; ρ, rocking; δ, scissoring; ss, symmetric stretching; ass, antisymmetric stretching; sb, symmetric bending; asb, antisymmetric bending; ipr, in-plane-rocking; opr, out-of-plane rocking

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