1H NMR of the 2-Amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline

¹H NMR of the 2-Amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline 5a





http://article.sapub.org/10.5923.j.chemistry.20140401.04.html

American Journal of Chemistry

p-ISSN: 2165-8749    e-ISSN: 2165-8781

2014;  4(1): 29-34

doi:10.5923/j.chemistry.20140401.04

Harvinder Singh Sohal¹, Rajshree Khare¹, Arun Goyal¹, Andrew Woolley², Kishanpal Singh³, Rajeev Sharma⁴

¹Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India

²Department of Chemistry, University of Toronto, 80 St. George St. Toronto, ON, M5S 3H6, Canada

³Department of Chemistry, Punjabi University, Patiala-147 001, Punjab, India

⁴Department of Chemistry, Multani Mal Modi College, Patiala-147 001, Punjab, India

Correspondence to: Harvinder Singh Sohal, Department of Chemistry, Maharishi Markandeshwar University, Mullana-133 207, Haryana, India.

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Multi-component Approach for the Synthesis of Fused Dihydropyridines via Unsymmetrical Hantzch Condensation Using Glycerol as Green Solvent

2-Amino-4-phenyl-3-cyano-7,7-dimethyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline (5a): 

mp. 277–278 °C; IR (KBr): ΰ = 3436, 3324, 3214, 2197, 1719, 1498 cm⁻¹. 

¹H NMR (400 MHz, CDCl₃): δ(ppm) = 1.02 (s, 3H, CH₃), 1.09 (s, 3H, CH₃), 2.01–2.37 (m, 4H, 2×CH₂), 4.38 (s, 1H, CH), 5.36 (s, 2H, NH₂), 7.07–7.29 (m, 5H, ArH), 8.94 (s, 1H, NH). 


¹³C NMR (100 MHz, CDCl₃): δ(ppm) = 27.4, 29.5, 32.8, 36.9, 39.4, 50.8, 59.7, 113.5, 119.7, 126.2, 127.8, 128.4, 143.9, 155.3, 166.3, 197.7.

MS (EI) m/z 294.3 (M+). 

Anal. Calcd for C₁₈H₁₉N₃O: C, 73.72; H, 6.48; N, 14.33. Found: C, 73.61; H, 6.58; N, 14.31.


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haryana

Sukhna Lake in Haryana

COSY , COSYDQF , Long-range COSY

COSY

This technique allows to observe a pulse spin-spin interaction constant of less than 1 Hz. 
This example shows the interaction of the aldehyde proton (17) and the protons of the methylene group (18,19) with the protons of the benzene ring.

LONG RANGE COSY






NOESY..........Correlation protons located close in space.






HXCORR

DOSY

Spectra allows to select individual compounds from mixtures, but only when a sufficient difference in the diffusion coefficients

SWEDEN

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APT (Attached Proton Test)

APT (Attached Proton Test)

Analogue techniques DEPT, but unlike it allows us to observe signals of quaternary carbon atoms (a)

DEPT (Distortionless Enhancement by Polarization Transfer)

Allow to distinguish signals of quaternary carbon atoms, CH, CH 2 and CH 3 groups.

Experiment DEPT (Distortionless Enhancement by Polarization Transfer) allows to distinguish between signals of quaternary, methine, methylene and methyl carbon atoms in the range of 13 C.

Depending on the multiplicity of the signals may be either positive or negative intensity. The most commonly used kind of experiment is DEPT DEPT135, in which the signals of the methylene carbon atoms - have negative intensity, methine and methyl - positive, and the signals of carbon atoms not directly associated with the protons do not appear. The spectrum exhibited only signals DEPT90 methine carbons and the spectrum DEPT45 quaternary carbons are not shown, and other signals - positive.

Experiment DEPT, usually used in conjunction with experiment 13 C with complete suppression of the spin-spin coupling (13 C { 1 H} experiment). From the analysis of the spectra of 13 C with suppression, DEPT135 and DEPT90 possible to draw conclusions about the multiplicity of all carbon atoms in the molecule.

As a result of polarization transfer to protons on the carbon atoms in the DEPT experiment of the sensitivity of the method is approximately four times greater than that of the standard experimental 13 C to complete suppression, and the experiment APT (Attached Proton Test).

DEPT experiment is less critical to the accuracy of selecting the value of direct constants C-H used to calculate a delay in the pulse sequence than experiment INEPT. This feature is useful in analyzing the structure containing carbon atoms of different natures, CH constants which respectively vary widely.

13C {1H} INVGATE

Spectra of the nuclei X decoupled from protons, but without signal amplification due to the nuclear Overhauser effect. In this case, the integral intensities of the signals is proportional to the amount of the corresponding nuclei H.

Spectra of the nuclei X decoupled from protons, where X - the core of the band 31 P- 15 N or 19 F. Provide information on the chemical shifts and the integrated intensity of the signal for the nuclei X.







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