Benjamin A. Smit-Colbran et al. “Nucleophilicity of reactive species through competition reactions: a demonstration with N-heterocyclic carbenes.” ChemRxiv (). https://doi.org/10.26434/chemrxiv.15006690/v2

5-((3,5-Di-tert-butyl-4-hydroxyphenyl)(4-methoxyphenyl)methyl)-4-(4-methylphenyl)-1,3-diphenyl-1,2,4-triazolium chloride
Identifier [1a• 2δ]•HCl
HR-MS (ESI) m/z: 634.36270 (M⁺,100 %). C₄₃H₄₄N₃O₂⁺ requires m/z: 634.34280 (M⁺, 100 %)
¹H NMR (600 MHz, DMSO-d₆) δ 7.00 (d, J = 8.7 Hz, 2H, C3′′′′-H), 6.76 (d, J = 8.7 Hz, 2H, C2′′′′-H), 6.67 (s, 2H, C2′′′′′-H), 5.90 (s, 1H, C6-H), 3.71 (s, 3H, C5′′′′-H), 2.29 (s. 3H, C7′′-H), 1.21 (s, 18H, C6′′′′′)
¹³C NMR (151 MHz, DMSO-d₆) δ 158.8 (C4′′′′), 155.5 (C5), 153.6 (C4′′′′), 141.3 (C4′′), 138.9 (C3′′′′′), 130.7 (C3′′), 130.5 (C3′′′′), 126.4 (C3′′′′′), 114.4 (C2′′′′), 55.3 (C5′′′′), 47.5 (C6), 34.4 (C5′′′′′), 30.1 (C6′′′′′), 21.0 (C5′′)
SI, p. 4
5-((3,5-Di-tert-butyl-4-hydroxyphenyl)(4-nitrophenyl)methyl)-4-(4-fluorophenyl)-1,3-diphenyl-1,2,4-triazolium chloride
Identifier [1c• 2α]•HCl
HR-MS (ESI) m/z: 640.34449 (M⁺,100 %). C₄₂H₄₃FN₃O₂⁺ requires m/z: 640.33338 (M⁺, 100 %)
¹H NMR (600 MHz, DMSO-d₆) δ 7.99 (d, J = 8.9 Hz, 2H, C3′′′-H), 7.68 – 7.74 (m, 1H, C2′′-H), 7.49 (t, J = 7.3 Hz, 1H, C4′-H or C4′′-H), 7.37 – 7.48 (m, 9H, C2′-H, C2′′-H, C2′′′-H, C6′-H, C6′′-H and C3′,C5′-H or C3′′,C5′′-H and C4′-H or C4′′-H), 7.34 (t, J = 7.8 Hz, 2H, C3′,C5′-H or C3′′,C5′′-H), 7.24 (ddd, JHF = 8.5 Hz, JHH = 8.5 Hz, ⁴JHH = 2.9 Hz, C3′′-H) 7.16 - 7.19 (m, 1H, C6′′-H), 7.02 (ddd, JHF = 8.5 Hz, JHH = 8.5 Hz, ⁴JHH = 2.9 Hz, C5′′-H), 6.65 (s, 2H, C2′′′′′-H), 6.27 (s, 1H, C6-H), 1.17 (s, 18H, C6′′′′′-H)
¹³C NMR (151 MHz, DMSO-d₆) δ 163.4 (C4′′, ¹JCF = 250.3 Hz), 154.6 (C5), 154.3 (C4′′′′′), 147.3 (C4′′′′), 143.8 (C1′′′′), 139.3 (C3′′′′′), 132.6 (C4′ or C4′′) 131.24 (C1′′′′′), 131.15 (C2′′, ³JCF = 9.8 Hz), 131.0 (C6′′, ³JCF = 9.8 Hz), 128.7 (C1′′, JCF = 3.3 Hz), 127.4 (C2′′′′′), 124.0 (C3′′′′), 117.6 (C3′′, ²JCF = 23.3 Hz), 117.3 (C5′′, ²JCF = 23.7 Hz), 48.5 (C6), 34.9 (C5′′′′′), 30.4 (C6′′′′′)
SI, p. 8
5-((3,5-Di-tert-butyl-4-hydroxyphenyl)(4-methoxyphenyl)methyl)-4-(4-bromophenyl)-1,3-diphenyl-1,2,4-triazolium chloride
Identifier [1d• 2γ]•HCl
HR-MS (ESI) m/z: 684.24041 (M⁺,100 %). C₄₂H₄₃BrN₃O₂⁺ requires m/z: 684.25840 (M⁺, 100 %)
¹H NMR (600 MHz, DMSO-d₆) δ 7.21 (m, 2H, C2′′′′), 7.12 (m, 2H, C3′′′′), 6.64 (s, 2H, C2′′′′′), 6.02 (s, 1H, C6), 2.25 (s, 3H, C5′′′′′), 1.21 (s, 18H, C6′′′′′)
¹³C NMR (151 MHz, DMSO-d₆) δ 155.1 (C5), 153.4 (C4′′′′′), 139.9 (C1′′′′), 138.5 (C3′′′′′), 136.0 (C4′′′′), 132.6 (C1′′′′′), 128.8 (C3′′′′), 126.4 (C2′′′′′), 126.1 (C2′′′′), 48.6 (C6), 34.3 (C5′′′′′), 29.3 (C6′′′′′), 20.7 (C5′′′′)