Simple and efficient synthesis with theoretical calculations of novel N-halamine monomers

Figures & data

Figure 1. Structures of synthesized styrenic monomers.

Figure 2. Scheme of the N-alkylation reaction leading to monomers.

Figure 3. B3LYP/6-311G(d,p) optimized structures of investigated synthesis.

Table 1. IR frequencies for N–H and C=O stretching vibrations [cm⁻¹] from experiment and PCM/B3LYP/6-311G(d,p) calculations for structures presented in Figure 4.

	Compound
Vibration [cm^−1]	1		2		3		4		5		6
	Exp.	Calc.	Exp.	Calc.	Exp.	Calc.	Exp.	Calc.	Exp.	Calc.	Exp.	Calc.
N–H stretch	3262	3250	3194	3230	3242	3249	3296	3225	3300	3252	3366	3222
		3138		3116		3116
C=O	1775	1786	1770	1782	1784	1782	1772	1789	1775	1814	1772	1792
	1715	1736	1730	1736	1720	1735	1710	1726	1714	1759	1716	1727

Table 2. ¹H NMR chemical shifts [ppm] for investigated compounds from experiment and PCM/B3LYP/6-311G(d,p) calculations for structures presented in Figure 4.

Chemical shift [ppm]	Compound
	1		2		3		4		5		6
	Exp.	Calc.	Exp.	Calc.	Exp.	Calc.	Exp.	Calc.	Exp.	Calc.	Exp.	Calc.
N–H	8.43 10.74	9.46 11.52	8.40 10.74	10.03 11.84	8.30 10.70	9.79 11.86	8.50	9.78	8.55	10.39	8.40	10.22
CHAr	–	–	7.23	7.50	7.12	7.37	7.20	7.35	7.22	7.33	7.01	7.31
				7.48		7.43	7.44	7.70	7.36	7.49	7.19	7.32
				7.53		7.44		7.98		7.54	7.41	7.43
								8.11		7.51		7.46
										7.50		7.90
										7.83		8.10
										8.08		8.48
										8.78
CH3	1.31	0.86	–	–	–	–	1.31	0.70	–	–	–	–
		1.05						0.97
		1.12						1.14
		1.28						1.24
		1.44						2.02
		2.34						2.08
CH2	–	–	3.08	2.76	1.83	1.48	4.52	4.35	3.02	2.93	1.83	1.77
			3.37	3.03	1.93	2.73		4.74	3.60	3.04	1.85	2.10
				3.59	2.78	2.85			4.66	3.42	2.82	2.62
				4.72	2.89	2.97				3.60	2.90	2.94
					3.11	3.15				4.68	3.10	3.23
						3.33				5.02	4.52	3.26
												4.64
												5.48
H2C	–	–	–	–	–	–	5.25	5.56	5.23	5.53	5.26	5.53
							5.82	6.28	5.72	6.25	5.72	6.25
HC=	–	–	–	–	–	–	6.72	6.89	6.68	6.89	6.72	6.89

Figure 4. Complexes of investigated systems with explicit DMSO molecules.