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INTERPRETATION OF NMR SPECTRUM

BYManish Kr.Gautam Research Scholar Pharmaceutical Chemistry
TEERTHANKER MAHAVEER COLLEGE OF PHARMACY

TEERTHANKER MAHAVEER UNIVERSITY MORADABAD (U.P.) INDIA

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INTERPRETATION OF NMR SPECTRA NMR spectrum of a substance gives very valuable information about its molecular structure this information is gathered as follows: 1:- The number of signals in the pmr spectrum tells us how many kinds of proton in different chemical environments are presents in the structure under examination. 2:- The position of signal tells us about the electronic environment of each kind of protons. 3:- The intensities of different signals tell us about the relative number of proton f different kinds. 4: The splitting of signals tells us about the environment of the absorbing proton with respect to the environments of the neighbouring proton. Note:In the case of signal where splitting takes places, the position of the signal is judged from the centre of doublet, triplet, etc. USEFUL GENERALISATION ABOUT THE POSITION OF SIGNAL: The position of the signal due to different kinds of proton but the following generalization about the environment of a proton and position of its absorption signal can be quite useful in the interpretation of nmr spectra. 1:- protons of a saturated carbon () not attached to hetero atom (h,o, halogen atom ) or unsaturated carbon atom absorbs in the region = ( 0.9--1.5) 2:-proton on a saturated carbon which is attached to a heteroatom or unsaturated carbon atom absorb in the region = (1.5--4.5) [H-C-O-] [H-C-C=C-] [H-C-N-] [H-C-C=O] [H-C-X] (X= F, Cl, Br, I) [H-C-CC-]

3:- Acetylenic protons (-CC-H) absorb at region = (2--3)

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4: Vinylic protons ( -HC=CH2) absorb at region = (4.6--5.6) 5:- Aromatic protons (Ar -H) absorbs at region = ( 68.5) 6: - Alcohal hydroxyl protons (R-OH) absorb at region = (1-1.5) H 7:- Aldehyde protons (-C=O) absorb at region = (9-10 ) 8:- Carboxylic protons (-COOH) absorb at region = (10.5-12) FOLLOWING POINT REGARDING THE SHIFT VALUE OF CHEMICAL

1:- Tau() value of methyl ,methylene , methyne proton have the order () = Methyl > Methylene > Methyne ( = Methyne < Methylene < Methyl

()

1 -----

2:- Tau() value depend upon the nature of the substitution on the carbon bearing the proton , greater the electronegativity of the substituent, lower is the value of tau () .

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3:- the value of tau () depend upon the type of the hybrid orbital holding the proton .

()

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()

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4- The tau () value for aromatic proton is always less than the 4 ppm. The value depends upon the degree and the nature of substituent. 5:- Tau () value for the aldehydic proton are generally lower ( 0.8 ppm or lower ) 6:- tau () value of proton in a cyclic compound is always higher than that of any other proton. The set of proton in cyclpropane has the maximum tau () value. 7:- the chemical shift of proton in (-OH) group & also in (-NH2) group depend upon the temperature , solvent, concentration , & the neighbouring group. Like that the alcohalic (-OH) proton gives a singlet at (4.5-9.0) (), the phenolic oh absorbs at( 2 TO 6.0 ) (). If (C=O) group is present in the ortho positon in phenol, then due to intramolecula hydrgen bonding , absorption occurs even at negative value of tau (). The -OH proton in the enolic form absorbs at (-4 TO -5) (). 8-The absorption due to COOH group appear at (-5.0 TO -2.0) () (10.5-12) B:- The number of signals in NMR spectrum tells us the number of the proton in different chemical environments. C:- it also tells the number of environment proton causing the splitting of a signal

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LETS US CONSIDER A FEW CASES : A:- in a spectrum , two signal, say Singlets are observed. This spectrum can be interpreted by saying that there are two kinds of proton and the two carbon atom carrying the two sets of proton are not the adjacent carbon atoms otherwise splitting of the signal would have taken place.

B:-The spectrum consisting of one doublet & one triplet must be due to the molecule having (-CH2-CH2-) as it part C:- Formation of two triplet must be due to two methylene group whose proton are in different environment. [X-CH2-CH2 - Y] D:-The formation of a singlet & a doublet must be due to [(CH3)2-CH] group which form a part of the molecule & so on. From the intensities of signal (peak areas) the ratio between different kinds of protons can be founds.