Predicting Heats of Explosion of Nitroaromatic Compounds through NBO Charges and 15N NMR Chemical Shifts of Nitro Groups

Table 1

Absolute energies, code designations, 𝑅_C−NNitro bond distances, nitro charges (𝑄_Nitro), ¹⁵N_Nitro NMR calculated chemical shifts, and experimental and calculated heats of explosion for nitroaromatic compounds used to build a quantitative model.

Number	Chemical name	Code designation	Energy^a (hartrees)	Distance 𝑅C−NNitro (Å)	NBO^b charge –𝑄Nitro	Calculated^c  15NNitro (ppm)	Experimental HE (H2O liq.) (MJ kg^−1)	Calculated^d HE (MJ kg^−1)
1	Tetryl	TETRYL	−1145	1.48604	0.191	−26.6	4.773	4.643
2	2,3,4,6-Tetranitroaniline	TeNA	−1105	1.47980	0.206	−25.6	4.378	4.336
3	2,4,6,2,4,6-hexanitrodiphenylamine	HNDP	−1746	1.48079	0.210	22.8	4.075	4.099
4	Ethyl tetryl	EtTETRYL	−1185	1.48692	0.214	−23.1	4.058	4.052
5	2,4,6-Trinitrobenzoic acid	TNBA	−1035	1.48776	0.215	−23.6	3.964	4.066
6	2,4,6-Trinitrophenoxethyl nitrate	TNPHN	1280	1.48143	0.213	−21.3	3.911	3.959
7	Methyl picrate	MePi	−960	1.47516	0.222	−19.4	3.777	3.695
8	Ethyl picrate	EtPi	−999	1.47720	0.225	−19.1	3.515	3.628
9	2,4-Dinitrotoluene	24DNT	−681	1.48113	0.248	−15.7	3.192	3.043
10	2,4,6-Trinitrophenol (picric acid)	PiAc	−921	1.47425	0.228	−18.6	3.437	3.524
11	2,4,6-Trinitrocresol	TNC	−961	1.47516	0.231	−17.6	3.370	3.438
12	Dinitro-ortho-cresol	DNoC	−756	1.47521	0.244	14.4	3.027	3.029
13	meta-Dinitrobenzene	mDNB	−641	1.48414	0.250	9.5	2.666	2.632
							RMSEP	0.0817

^aCalculated with B3LYP/6-311+G(d,p); ^bnatural bond orbital analysis; ^ccalculated with CSGT-B3LYP/6-311+G(2d,p); ^dpredicted by (1).