NMR Discussion

These NMR spectra are scaled to 80mm height.

1,4-di(4-chlorophenyl)-1,4-diazabutadiene

C₁₄H₁₀Cl₂N₂ 277.15gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 8.35 (s, 2H), 7.41 (dt, J=2Hz, J=9Hz, 4H), 7.24 (dt, J=8.75Hz, J=2.2Hz).

¹³C-NMR (400MHz, CDCl₃) δ 160.29, 148.78, 134.23, 130.03, 123.05.

 

1,4-di(tert-butyl)-1,4-diazabutadiene

C₁₀H₂₀N₂ 168.28gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 7.95 (s, 2H), 1.27 (s, 18H).

¹H-NMR (400MHz, D₂O) δ 4.69 (s, 18H),

¹³C-NMR (400MHz, CDCl₃) δ 157.85, 58.17, 29.36.

 

Imidazole

C₃H₄N₂ 68.08gmol^-1

White crystals soluble with water and moderately soluble in chloroform. The 4(5)- protons are equivalent.

¹H-NMR (400MHz, CDCl₃) δ 12.42 (s, 1H), 7.73 (s, 1H), 7.13 (s, 1H)

¹H-NMR (400MHz, D₂O) δ 10.13 (s, 1H), 9.50 (s, 2H), 7.23 (s, 2H)

¹³C-NMR (400MHz, CDCl₃) δ 135.24, 121.87

 

1-methylimidazole

C₄H₆N₂ 82.10gmol^-1

A slight tan viscous liquid miscible with both water and chloroform.

¹H-NMR (400MHz, CDCl₃) δ 7.42 (s, 1H), 7.04 (s, 1H), 6.88 (s, 1H), 3.66 (s, 3H)

 

¹H-NMR (400MHz, D₂O) δ 7.38 (s, 1H), 6.87 (s, 1H), 6.80 (s, 1H), 3.48 (s, 3H)

¹³C-NMR (400MHz, D₂O) δ 138.37, 127.44, 121.18, 32.84

¹H-NMR (400MHz, MeOD) δ 7.6 (s, 1H), 7.08 (s, 1H), 6.97 (s, 1H), 3.74 (3H)

1-methyl-3-ethoxymethyl-imidazolium chloride

C₇H₁₃N₂OCl 176.64gmol^-1

¹H-NMR (400MHz, D₂O) δ 8.83 (s, 1H), 7.51 (s, 1H), 7.41 (s, 1H), 5.48 (s, 2H), 3.83 (s, 3H), 3.545 (q, J=7.04Hz, 2H), 1.09 (t, J=7.04Hz, 3H)

¹³C-NMR (400MHz, D₂O) δ 136.34, 124.06, 121.60, 78.22, 65.99, 35.86, 13.81

1-hydroxymethylimidazole

C₄H₆N₂O 98.10gmol^-1

A waxy solid soluble in chloroform, acetonitrile and dichloromethane. * Reacts with water.

¹H-NMR (400MHz, CDCl₃) δ 8.49 (s, 1H), 7.37 (s, 1H), 7.06 (s, 1H), 6.91 (s, 1H),

5.39 (s, 2H)

¹³C-NMR (400MHz, CDCl₃) δ 128.50, 127.46, 125.42, 70.37, 25.16

Glyoxal trimer dehydrate

C₆H₁₀O₈ (210.14gmol^-1)

¹H-NMR (400MHz, CDCl₃) δ 1.55 (s, 6H)

Methylene sulphate*

(CH₂O₄S)_n 110.09gmol^-1 *may be a dimer or polymer

 

1-chloromethylimidazole

C₄H₅N₂Cl 116.55gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 7.45 (s, 1H), 7.39 (s, 1H), 7.31 (s, 1H), 6.10 (s, 2H)

Bis(imidazolyl)methane

C₇H₈N₄ 148.17gmol^-1

White crystal plates poorly soluble in water and chloroform.

¹H-NMR (400MHz, D₂O) δ 7.75 (s, 2H), 7.09 (s, 2H), 6.87 (s, 2H), 6.06 (s, 2H)

¹H-NMR (400MHz, CDCl₃) δ 7.66 (s, 2H), 7.12 (s, 2H), 7.00 (s, 2H), 6.00 (s, 2H)

¹³C-NMR (400MHz, D₂O) δ 137.64, 128.77, 119.28, 55.96

¹³C-NMR (400MHz, CDCl₃) δ 136.60, 131.18, 118.10, 56.33

Bis(1-methylimidazolium-3-yl)methane chloride

C₉H₁₄Cl₂N₄ 249.14gmol^-1

¹H-NMR (400MHz, D₂O) δ 7.64 (s, 2H), 7.47 (s, 2H), 6.58 (s, 2H), 3.84 (s, 6H)

¹³C-NMR (400MHz, D₂O) δ

 

 

Benzil

C₁₄H₁₀O₂ 210.23gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 7.97 (t, J=7.92Hz, 4H), 7.65 (t, J=7.34Hz, 2H), 7.51 (t, J=7.58Hz, 4H)

¹³C-NMR (400MHz, CDCl₃) δ 194.60, 134.92, 132.98, 129.92, 129.04

 

1-methyl-3-chloromethylimidazolium chloride

C₅H₈Cl₂N₂ 167.04gmol^-1

2,4,6-trimethylaniline (mesidine)

C₉H₁₃N 135.21gmol^-1

A slightly red viscous oil. Miscible with chloroform.

¹H-NMR (400MHz, CDCl₃) δ 6.75 (s, 2H), 3.40 (s, 2H), 2.19 (s, 3H), 2.13 (s, 6H)

¹H-NMR (400MHz, D₂O) δ 7.13 (t, J=7.5Hz, 2H), 6.80-6.70 (m, 3H), 4.69 (s, 2H)

¹³C-NMR (400MHz, CDCl₃) δ 140.27, 128.95, 127.16, 121.91, 20.48, 17.67

1,2,4,5-tetraphenyl imidazole

C₂₇H₂₀N₂ 372.46gmol^-1

Insoluble in water, readily soluble in chloroform and acetone.

¹H-NMR (400MHz, CDCl₃) δ 7.60 (d, J=7.53Hz, 2H), 7.43 (d, J=7.24Hz, 2H), 7.30-7.15 (m, 12H), 7.13 (d, J=6.65Hz, 2H), 7.04 (d, J=6.94Hz, 2H)

¹³C-NMR (400MHz, CDCl₃) δ

Benzaldehyde

C₇H₆O 106.12gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 10.02 (s, 1H), 7.88 (d, J=7.92Hz, 2H), 7.63 (t, J=7.3Hz, 1H), 7.53 (t, J=7.53Hz, 2H)

¹³C-NMR (400MHz, CDCl₃) δ 192.40, 136.39, 134.46, 129.73, 128.99

Aniline

C₆H₇N 93.13gmol^-1

A yellow-pink oil miscible with chloroform and very slightly soluble in water.

¹H-NMR (400MHz, CDCl₃) δ 7.13 (t, J=7.78Hz, 2H), 6.74 (t, J=6.34Hz, 1H), 6.64 (d, J=7.92, 2H), 3.58 (s, 2H)

¹³C-NMR (400MHz, CDCl₃) δ 146.52, 129.37, 118.57, 115.18

¹³C-NMR (400MHz, D₂O) δ 146.04, 129.44, 119.48, 116.37

 

4-chloroaniline

C₆H₆ClN 127.57gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 7.09 (d, J=8.31Hz, 2H), 6.59 (d, J=8.22Hz, 2H), 3.64 (s br, H).

¹H-NMR (400MHz, D₂O) δ 7.09 (d, J=8.61Hz, 2H), 6.69 (d, J=8.61Hz, 2H), 4.69 (s br, 2H).

¹³C-NMR (400MHz, CDCl₃) δ 144.99, 129.12, 123.12, 116.25.

1-(2,4,6-trimethylphenyl)imidazole

C₁₂H₁₄N₂ 186.25gmol^-1

1-methyl-3-(2,4,6-trimethylphenyl)imidazole

C₁₃H₁₇IN₂ 328.19gmol^-1

2,2,5,5-tetramethyl-3,4-hexandione

C₁₀H₁₈O₂ 170.25gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 1.16 (s, 18H).

¹³C-NMR (400MHz, CDCl₃) δ 209.40, 40.08, 24.50.

Cyclohexane-1,2-dione

C₆H₈O₂ 112.13gmol^-1

3,3,6,6-Tetramethyl cyclohexan-1,2-dione

C₁₀H₁₆O₂ 168.23gmol^-1

N,N’-dimethyl-N,N’-methoxy oxaldiamide

C₆H₁₂N₂O₄ 176.17gmol^-1

White needles very soluble in chloroform.

¹H-NMR (400MHz, CDCl₃) δ 3.25 (s, 6H), 3.74 (s, 6H)

1,4-dibromobutane

C₄H₈Br₂ 215.91gmol^-1

2,6-dimethyl hex-2,4-ene

C₈H₁₄ 110.20gmol^-1

2,6-dimethyl-2,6-dibromohexane

C₈H₁₆Br₂ 272.02gmol^-1

Chloroiodomethane

CH₂ClI 176.38gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 4.99 (s, 2H)

¹³C-NMR (400MHz, CDCl₃) 76.13 (t)

1,2-Dibromoethane

C₂H₄Br₂ 187.86gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 3.66 (s, 4H)

¹³C-NMR (400MHz, CDCl₃) δ 29.60

 

 

1,4-dibromobutane

C₄H₈Br₂ 215.91gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 3.45 (s, 2H), 2.04 (s, 2H)

¹³C-NMR (400MHz, CDCl₃) δ 32.59, 30.96

Diiodomethane

CH₂I₂ 267.84gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 3.89 (s, 2H)

Dichloromethane

CH₂Cl₂ 84.93gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 5.33 (s, 2H)

Chloromethyl ethyl ether

A dangerously carcinogenic liquid miscible with chloroform but decomposes on contact with water.

C₃H₇OCl 94.54gmol^-1

¹H-NMR (400MHz, CDCl₃) δ 5.52 (s, 2H), 3.76 (q, J=7.08, 2H), 1.27 (t, J=7.09, 3H)

¹³C-NMR (400MHz, CDCl₃) δ 82.99, 66.07, 14.39

1,3-dimesitylimidazolium chloride (IMes·Cl)

C₂₁H₂₅N₂Cl 340.89gmol^-1

¹H-NMR (249.87Mhz, CDCl₃): δ ppm 2.19 (s, 12H, o-CCH₃), 2.34 (s, 6H, p-CCH₃), 7.03 (s, 4H, m-H), 7.63 (s, 2H, NCH=CHN), 10.89 (s, 1H, NCHN). ¹³C-NMR (249.87Mhz, CDCl₃): δ ppm 17.67 [4C, o-CCH₃], 21.18 [2C, p-CCH₃], 124.37 [2C, NC=CN], 129.95 [4C, m-C], 130.63 [2C, p-C], 134.09 [4C, o-CCH₃], 139.81 [2C, i-CN], 141.36 [2C, NC=CN].

Bis(1,3-bismesityl-imidazol-3-ium-2-yl)argentate chloride

C₄₂H₅₀N₂AgCl 754.19gmol^-1

A chalky white solid insoluble in hexane but soluble in dichloromethane.

(1s)-1-phenylethanol

Soluble in chloroform.

¹H-NMR (400MHz, CDCl₃) δ 1.46 (d, J=6.5Hz, 3H), 2.18 (d, J=3.6Hz, 1H), 4.85 (qd, J=6.5Hz, 3.4Hz,1H), 7.30-7.36 (m, 5H)

(1R)-(−)-10-Camphorsulfonyl chloride

¹H-NMR (400MHz, CDCl₃) δ 0.93 (s, 3H), 1.14 (s, 3H), 1.49 (ddd, J=12.72Hz, 9.24Hz, 3.86Hz), 1.78 (ddd, J=13.96Hz, 9.37Hz, 4.65Hz, 3H), 2.00 (d, J=18.68Hz, 1H), 2.11 (m, J=16.18Hz, 8.13Hz, 3.94Hz, 3.94Hz, 1H), 2.17 (t, J=4.55Hz, 1H), 2.45 (m, 2H), 3.73 (d, J=14.57Hz, 1H), 4.31 (d, J=14.67Hz, 1H)

¹³C-NMR (400MHz, CDCl₃) δ 19.66, 19.77, 25.29, 26.88, 42.33, 42.79, 48.20, 59.71, 64.26, 212.81

 

1-methyl-3-benzyl imidazolium iodide

A light yellow crystalline solid

Solid is purified by trituration with 10% ethanol in ether. Material is reasonably soluble in spectroscopic grade CDCl₃ at RTP and very soluble in DMSO. In chloroform, the methyl protons (4.05ppm, 3H), the benzylic protons (5.58ppm, 2H) and the imidazolium C²-proton (9.98ppm, 1H) are identifiable as clear resonants. The imidazolium-4,5 protons (2H) are clustered in the phenyl aromatic region (5H) along with CHCl₃. Found 13H.

In DMSO, similarly distinct resonants are observed but far greater resolution is observed of the aromatic region. The phenyl proton resonants overlap in the form of a typical aromatic multiplet, but the imidazole-4,5 proton resontants (7.73ppm, 1H and 7.81ppm, 1H) are distinct.

1-allyl-3-methyl imidazolium iodide

A light yellow crystalline solid

Material is soluble in spectroscopic grade CDCl₃ at RTP and very soluble in DMSO. In chloroform, the methyl protons (4.14ppm, 3H), the allylic protons (5.04ppm, d, 2H), the imidazolium C²-proton (9.81ppm, 1H) and the imidazolium-4,5 protons (7.72 and 7.59, 2H) are identifiable as clear resonants. The terminal olefinic protons resonate at between 5.59 and 5.47ppm, m). The allyl methine resonance with a distinct multiplet (6.14-6.01ppm, m, 1H). Found 11H.

In DMSO, the imidazolium-4,5 protons are not distinct from one-another.

2-methylnaphthalene

Clear crystalline plates mp 34 – 36ºC

Material is soluble in spectroscopic grade CDCl₃ at RTP and very soluble in DMSO. In chloroform, the methyl protons are distinct (2.48ppm, 3H). The aromatic region is typical.

 2-bromomethylnaphthalene

A tan powder mp 49 – 51ºC

Material is soluble in spectroscopic grade CDCl₃ at RTP and very soluble in DMSO. In chloroform, the bromomethyl protons are distinct (4.66ppm, 2H). The aromatic region is typical. A conversion ratio of 90% is ascertained by comparison of the product 2-bromomethyl resonant integral and the starting material methyl resonant integral.

1-naphthyl-3-methyl imidazolium iodide

A light yellow crystalline solid

Material is soluble in spectroscopic grade CDCl₃ at RTP and very soluble in DMSO. In chloroform, the methyl protons (4.14ppm, 3H), the allylic protons (5.04ppm, d, 2H), the imidazolium C²-proton (9.81ppm, 1H) and the imidazolium-4,5 protons (7.72 and 7.59, 2H) are identifiable as clear resonants. The terminal olefinic protons resonance at between 5.59 and 5.47ppm, m). The allyl methine resonance with a distinct multiplet (6.14-6.01ppm, m, 1H). Found 11H.

2-naphthyl-3-methyl imidazolium iodide

A brown oil

 

1-(2-nitrobenzyl)-3-methyl imidazolium iodide

A clear crystalline solid

Material is soluble in spectroscopic grade CDCl₃ at RTP and very soluble in DMSO.

The peak at 3.71 represents an impurity of methylimidazole (it is congruent with the peaks at 7.06 and 6.90)

1-(para-methoxybenzyl)-3-methyl imidazolium bromide

Brown oil

May11-2009-LMH_250\001r

Material is soluble in spectroscopic grade CDCl₃ at RTP and very soluble in DMSO. In chloroform, the 3-methyl protons are present at a position typical for these compounds (4.06ppm, s, 3H), as are the methoxy protons typical of the PMB group (3.80ppm, s, 3H). The benzylic protons (5.49ppm, s, 2H) and the imidazolium C2 proton (10.07ppm, s, 1H) are clearly visible.