Product Distribution in the Nitration of Toluene

Steven W. Anderson

COMPLETE DATA

Table 3. Complete Energetic Data in the itration of Toluene

chemical sample	energy steric (kcal/mol)	energy total (Hartree)*	heat of formation (kcal/mol)	heat of reaction (overall) (kcal/mol)	heat of reaction (to arenium ions) (kcal/mol)
toluene	-8.597	-44.783	14.114
nitric acid+			-32.0999
water+			-57.8
o-nitrotoluene	-7.108	-76.581	8.067	-31.7471
ortho-1	2.581	-77.082	216.146		234.1319
ortho-2	2.858	-77.086	215.899		233.8849
ortho-3	1.886	-77.085	216.004		233.9899
m-nitrotoluene	-9.043	-76.592	5.092	-34.7221
meta-1	2.295	-77.077	218.415		236.4009
meta-2	2.747	-77.076	218.314		236.2999
meta-3	3.334	-77.074	218.308		236.2939
p-nitrotoluene	-9.061	-76.595	4.71	-35.1041
para-1	2.545	-77.096	213.369		231.3549
para-2	2.236	-77.096	213.349		231.3349
para-3	2.533	-77.096	213.367		231.3529

^*1 Hartree = 627.5 kcal/mol
⁺Data obtained from NIST Chemistry Webbook at: http://webbook.nist.gov/chemistry/

Table 4. Complete nucleophilic and electrophilic susceptibility data for toluene and arenium ions
chemical sample	atom	nucleophilic susceptibility	electrophilic susceptibility
toluene	C1	0.312	0.284
	C2	0.315	0.245
	C3	0.35	0.416
	C4	0.305	0.235
	C5	0.323	0.294
	C6	0.368	0.428
o-nitrotoluene	C2	0.435
	C4	0.269
	C6	0.329
ortho-1	C2	0.679
	C4	0.421
	C6	0.329
ortho-2	C2	0.678
	C4	0.421
	C6	0.621
ortho-3	C2	0.682
	C4	0.425
	C6	0.614
m-nitrotoluene	C1	0.449
	C3	0.296
	C5	0.293
meta-1	C1	0.718
	C3	0.515
meta-2	C1	0.723
	C3	0.524
	C5	0.511
meta-3	C1	0.717
	C3	0.52
	C5	0.526
p-nitrotoluene	C2	0.291
	C4	0.427
	C6	0.329
para-1	C2	0.48
	C4	0.469
	C6	0.774
para-2	C2	0.467
	C4	0.478
	C6	0.774
para-3	C2	0.46
	C4	0.488
	C6	0.774