chem-30b identification of organic and inorganic compounds by spectroscopy mass spectrometry nmr ...
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Chem-30BChem-30BIdentification of organic and inorganic Identification of organic and inorganic
compounds by spectroscopycompounds by spectroscopy
Mass SpectrometryNMRInfraredInfrared
InfraredInfrared10,000 cm10,000 cm-1-1 to 100 cm to 100 cm-1-1
Converted in Vibrational energy in moleculesConverted in Vibrational energy in molecules
Vibrational Spectra appears as bands instead of sharp lines => as it is accompanied by a number of rotational changes
Wave Number => (cm-1) => proportional to energy
Depends on:•Relative masses of atoms•Force constant of bonds•Geometry of atoms
Older system uses the wavelenght (m => 10-6 m)
cm-1 = 104 / m
The Units:The Units:The frequency (s-1) => # vibrations per second
For molecular vibrations, this number is very large (1013 s-1) => inconvenient
More convenient : Wavenumber = c
(Frequency / Velocity)
e.g. = 3 * 10 = 3 * 101313 s s-1-1
= s
3 * 1010 cm s-1
= 1000 cm= 1000 cm-1-1
Wave Length : 1
=
Intensity:Intensity: Transmittance (TT) or %T%T
TT =II0
Absorbance (AA)
AA = log II0
Intensity in IRIntensity in IR
IRIR : Plot of %IR%IR that passes through a sample (transmittancetransmittance) vs WavelenghtWavelenght
InfraredInfrared
• Position, Intensity and Shape of bands gives clues on Structure of molecules
• Modern IR uses Michelson Interferometer=> involves computer, and Fourier Transform
SamplingSampling => plates, polished windows, Films …Must be transparent in IR
NaCl, KCl : Cheap, easy to polishNaCl, KCl : Cheap, easy to polish
NaClNaCl transparent to 4000 - 650 cm4000 - 650 cm-1-1
KClKCl transparent to 4000 - 500 cm4000 - 500 cm-1-1
KBr KBr transparent to 400 cm400 cm-1-1
Infrared: Low frequency spectra of Infrared: Low frequency spectra of window materialswindow materials
Bond length and strength Bond length and strength vs vs
Stretching frequencyStretching frequency
Bond C-H =C-H -C-H
Length 1.08 1.10 1.12
Strenght 506 kJ 444 kJ 422 kJ
IR freq. 3300 cm-1 3100 cm-1 2900 cm-1
IntroductionIntroduction
IR is one of the first technique inorganic chemists used (since 1940)
Molecular VibrationMolecular Vibration
Newton’s law of motion is used classically to calculate force constant
r
reFFFF The basic picture : atoms (mass) are
connected with bonding electrons. Re is the equilibrium distance and FF: force to restore equilibrium
F(x) = -kx where X is displacement from equilibrium
= = 11
22 √kkiiii
Where Where KKii is the force constant and is the force constant and ii is reduce mass of a particular motionis reduce mass of a particular motion
Because the energy is quantized: E = Because the energy is quantized: E = h h ii
IntroductionIntroduction
Displacement of atoms during vibration lead to distortion of Displacement of atoms during vibration lead to distortion of electrival charge distribution of the molecule which can be resolve electrival charge distribution of the molecule which can be resolve in dipole, quadrupole, octopole …. In various directionsin dipole, quadrupole, octopole …. In various directions
=> Molecular vibration lead to oscillation of electric charge => Molecular vibration lead to oscillation of electric charge governed by vibration frequencies of the systemgoverned by vibration frequencies of the system
Oscillating molecular dipole can interact directly with oscillating Oscillating molecular dipole can interact directly with oscillating electric vector of electromagnetic radiation of the same frequencyelectric vector of electromagnetic radiation of the same frequency
h h = = hh
Vibrations are in the range Vibrations are in the range 10101111 to 10 to 101313 Hz Hz => => 30 - 3,000 cm30 - 3,000 cm-1-1
Introduction: Symmetry selection ruleIntroduction: Symmetry selection rule
Stretching homonuclear diatomic molecule likeStretching homonuclear diatomic molecule like N N22 does not does not
generate oscillating dipolegenerate oscillating dipole Direct interaction with oscillating electronic Dipole is not possibleDirect interaction with oscillating electronic Dipole is not possible inactive in IRinactive in IR
There is no place here to treat fundamentals of symmetryThere is no place here to treat fundamentals of symmetryIn principle, the symmetry of a vibration need to be determinedIn principle, the symmetry of a vibration need to be determined
VibrationsVibrationswww.cem.msu.edu/~reusch/Virtual/Text/Spectrpy/InfraRed/infrared.htm
Modes of vibrationModes of vibrationCC—H—HStretchingStretching
BendingBending CC
OO
HH
H
H
Symmetrical Symmetrical 2853 cm2853 cm-1-1
H
H
Asymmetrical Asymmetrical 2926 cm2926 cm-1-1
H
H
H
H
ScissoringScissoring1450 cm1450 cm-1-1
RockingRocking720 cm720 cm-1-1
HH
HH
WaggingWagging1350 cm1350 cm-1-1
TwistingTwisting1250 cm1250 cm-1-1
StretchingStretchingfrequencyfrequency
BendingBendingfrequencyfrequency
VibrationsVibrationswww.cem.msu.edu/~reusch/Virtual/Text/Spectrpy/InfraRed/infrared.htm
General trends:General trends:•Stretching frequenciesStretching frequencies are higher than are higher than bending frequencies bending frequencies (it is easier to bend a bond than stretching or compresing them)(it is easier to bend a bond than stretching or compresing them)
•Bond involving Hydrogen are higher in freq. than with heavier atomsBond involving Hydrogen are higher in freq. than with heavier atoms
•Triple bondTriple bond have higher freq than have higher freq than double bonddouble bond which has higher freq which has higher freq than than single bondsingle bond
Structural Information from Vibration SpectraStructural Information from Vibration Spectra
• Spectrum can be treated as finger print to recognize Spectrum can be treated as finger print to recognize the product of a reaction as a known compound. the product of a reaction as a known compound. (require access to a file of standard spectra)(require access to a file of standard spectra)
• At another extreme , different bands observed can be At another extreme , different bands observed can be used to deduce the symmetry of the molecule and force used to deduce the symmetry of the molecule and force constants corresponding to vibrations.constants corresponding to vibrations.
• At intermediate levels, deductions may be drawn about At intermediate levels, deductions may be drawn about the presence/absence of specific groupsthe presence/absence of specific groups
The symmetry of a molecule determines the number of bands expectedThe symmetry of a molecule determines the number of bands expected
Number of bands can be used to decide on symmetry of a moleculeNumber of bands can be used to decide on symmetry of a molecule
Tha task of assignment is complicated by presence of low intensity bands and Tha task of assignment is complicated by presence of low intensity bands and presence of forbidden overtone and combination bands.presence of forbidden overtone and combination bands.There are different levels at which information from IR can be analyzed to There are different levels at which information from IR can be analyzed to allow identification of samples:allow identification of samples:
Methods of analyzing an IR spectrumMethods of analyzing an IR spectrum
The effect of The effect of isotopic substitutionisotopic substitution on the observed spectrum on the observed spectrumCan give valuable information about the atoms involved in a Can give valuable information about the atoms involved in a particular vibrationparticular vibration
1.1. Comparison with standard spectra : traditional approachComparison with standard spectra : traditional approach
2.2. Detection and Identification of impuritiesDetection and Identification of impuritiesif the compound have been characterized before, any bands that are not found in the pure sample can be assigned to the impurity (provided that the 2 spectrum are recorded with identical conditions: Phase, Temperature, Concentration)
3.3. Quantitative Analysis of mixtureQuantitative Analysis of mixtureTransmittance spectra = I/I0 x 100 => peak height is not lineraly related to intensity of absorptionIn Absorbance A=ln (Io/I) => Direct measure of intensity
Analyzing an IR spectrumAnalyzing an IR spectrum
In practice, there are similarities between frequencies of molecules In practice, there are similarities between frequencies of molecules containing similar groups.containing similar groups.
Group - frequency correlationsGroup - frequency correlations have been extensively developed for have been extensively developed for organic compounds and some have also been developed for organic compounds and some have also been developed for inorganicsinorganics
Symmetrical and asymmetrical stretch Symmetrical and asymmetrical stretch
MethylMethyl 2872 cm2872 cm-1-1
Symmetrical StretchSymmetrical Stretch Asymmetrical StretchAsymmetrical Stretch
——CC——HH
HH
HH
——CC——HH
HH
HH
AnhydrideAnhydrideOO
OO OO1760 cm1760 cm-1-1
2962 cm2962 cm-1-1
1800 cm1800 cm-1-1
OO
OO OO
AminoAmino
NitroNitro
——NNHH
HH3300 cm3300 cm-1-1
3400 cm3400 cm-1-1
1350 cm1350 cm-1-1 1550 cm1550 cm-1-1
——NNHH
HH
——NN
OO
OO——NN
OO
OO
General IR commentsGeneral IR commentsPrecise treatment of vibrations in molecule is not feasible herePrecise treatment of vibrations in molecule is not feasible hereSome information from IR is also contained in MS and NMRSome information from IR is also contained in MS and NMR
Certain bands occur in Certain bands occur in narrow regionsnarrow regions : : OHOH, , CHCH, , C=OC=O
Detail of the structure is revealed by the Detail of the structure is revealed by the exact positionexact position of the band of the band
e.g. e.g. KetonesKetonesO
1715 cm1715 cm-1-1
CH
O
CH2
1680 cm1680 cm-1-1
Region 4000 – 1300 : Functional groupRegion 4000 – 1300 : Functional group
Absence of band in this region can be used to deduce absence of groupsAbsence of band in this region can be used to deduce absence of groupsCaution: some bands can be very broad because of hydrogen bonding Caution: some bands can be very broad because of hydrogen bonding
e.g. e.g. Enols v.broad OH, C=O absent!!Enols v.broad OH, C=O absent!!
Weak bands in high frequency are extremely useful : S-H, CWeak bands in high frequency are extremely useful : S-H, CC, CC, CNN
Lack of strong bands in 900-650 means no aromaticLack of strong bands in 900-650 means no aromatic
AlkanesAlkanes, , AlkenesAlkenes, , AlkynesAlkynes
C-H : C-H : <3000 cm<3000 cm-1-1 >3000 cm>3000 cm-1-1 3300 cm3300 cm-1-1 sharpsharp
C-CC-C
StretchStretch
Not usefulNot useful
C=CC=C
CCCC
1660-1600 cm1660-1600 cm-1-1
conj. Moves to lower valuesconj. Moves to lower values Symmetrical : no bandSymmetrical : no band
2150 cm2150 cm-1-1
conj. Moves to lower valuesconj. Moves to lower valuesWeak but very usefulWeak but very useful
Symmetrical no bandSymmetrical no band
BendingBending CHCH2 2 RockingRocking
720 cm720 cm-1 -1 indicateindicatePresence of 4-CHPresence of 4-CH2 2
1000-700 cm1000-700 cm-1-1 Indicate substitutionIndicate substitution
patternpattern
C-H ~630 cmC-H ~630 cm-1-1 Strong and broadStrong and broad
Confirm triple bondConfirm triple bond
Alkene : Alkene : 1-Decene1-Decene
To give rise to absorption of IRTo give rise to absorption of IR => Oscillating Electric DipoleOscillating Electric DipoleSymmetrySymmetry
Molecules with Center of symmetryMolecules with Center of symmetrySymmetric vibration => inactiveSymmetric vibration => inactiveAntisymmetric vibration => activeAntisymmetric vibration => active
AlkeneAlkene
In large molecule local symmetry produce In large molecule local symmetry produce weak or absent vibrationweak or absent vibration
C=CC=CRR
RRtranstrans C=C isomer -> weak in IR C=C isomer -> weak in IR
Observable in RamanObservable in Raman
Alkene: Factors influencing vibration frequencyAlkene: Factors influencing vibration frequency1- Strain move peak to right (decrease )1- Strain move peak to right (decrease )
CCCCCC
angleangle
16501650 16461646 16111611 156615661656 : exception1656 : exception
2- Substitution increase2- Substitution increase
3- conjugation decrease3- conjugation decrease C=C-Ph 1625 cmC=C-Ph 1625 cm-1-1
15661566 16411641 16751675
16111611 16501650 16791679
16461646 16751675 16811681
Alkene: Out-of-Plane bending Alkene: Out-of-Plane bending
This region can be used to deduce substitution patternThis region can be used to deduce substitution pattern
In IR, Most important transition involve :In IR, Most important transition involve :
Ground State (Ground State (i i = 0) = 0) to to First Excited State (First Excited State (i = 1)i = 1)
TransitionTransition ((i i = 0) = 0) to to ((JJ = 2) = 2) => Overtone => Overtone
IR : AromaticIR : Aromatic
=C-H=C-H > 3000 cm> 3000 cm-1-1
C=CC=C 1600 and 1475 cm1600 and 1475 cm-1-1
=C-H=C-H out of plane bending: great utility to assign ring substitutionout of plane bending: great utility to assign ring substitution
overtoneovertone 2000-1667: useful to assign ring substitution2000-1667: useful to assign ring substitution
e.g. Naphthalene: e.g. Naphthalene: Substitution patternSubstitution pattern Isolated HIsolated H 862-835862-835
835-805835-805
760-735760-735
2 adjacent H2 adjacent H
4 adjacent H4 adjacent H
out of plane bendingout of plane bending
IR: Alcohols and PhenolsIR: Alcohols and Phenols
O-H Free : Sharp 3650-3600O-H Free : Sharp 3650-3600
O-H H-Bond : Broad 3400-3300O-H H-Bond : Broad 3400-3300
Intermolecular Hydrogen bonding Increases with concentration=> Less “Free” OHLess “Free” OH
IR: Alcohols and PhenolsIR: Alcohols and Phenols
C-O : 1260-1000 cmC-O : 1260-1000 cm-1-1 (coupled to C-C => C-C-O) (coupled to C-C => C-C-O)
C-O Vibration is sensitive to substitution:C-O Vibration is sensitive to substitution:
PhenolPhenol 122012203` Alcohols3` Alcohols 115011502` Alcohols2` Alcohols 110011001` Alcohols1` Alcohols 10501050
More complicated than above: shift to lower Wavenumber More complicated than above: shift to lower Wavenumber With unsaturation (Table 3.2)With unsaturation (Table 3.2)
Benzyl AlcoholBenzyl Alcohol
OHOH spsp22spsp33
PhPhovertoneovertone
C-O : 1080, 1022 cmC-O : 1080, 1022 cm-1 -1 : primary OH: primary OH
MonoMonoSubst. PhSubst. Ph735 & 697 cm735 & 697 cm-1-1
PhenolPhenol
OHOH spsp22
PhPhovertoneovertone
C=C stretchC=C stretch
Ph-O : 1224 cmPh-O : 1224 cm-1-1
MonoMonoSubst. PhSubst. Phout-of planeout-of plane810 & 752 cm810 & 752 cm-1-1
IR: EtherIR: EtherC-O-CC-O-C =>=> 1300-1000 cm1300-1000 cm-1-1
Ph-O-C Ph-O-C =>=> 1250 and 1040 cm1250 and 1040 cm-1-1
AliphaticAliphatic => => 1120 cm1120 cm-1-1
C=C in vinyl Ether C=C in vinyl Ether => => 1660-1610 cm1660-1610 cm-1-1
appear as Doublet => rotational isomersappear as Doublet => rotational isomers
CH2 CH
O CH3
~1620~1620
~1640~1640
H2C CH
O CH3
H2C CH
O
CH3
EtherEther
spsp22
spsp33
PhPhovertoneovertone
C=C stretchC=C stretch
Ph-O-C : 1247 cmPh-O-C : 1247 cm-1-1 Asymmetric stretch Asymmetric stretchPh-O-C : 1040 cmPh-O-C : 1040 cm-1-1 Symmetric stretch Symmetric stretch
MonoMonoSubst. PhSubst. Phout-of planeout-of plane784, 754 & 692 cm784, 754 & 692 cm-1-1
O
H
CH
CH3
CH3
CH3
O
IR: CarbonylIR: Carbonyl From 1850 – 1650 cmFrom 1850 – 1650 cm-1-1
Ketone 1715 cmKetone 1715 cm-1-1 is used as reference point for comparisons is used as reference point for comparisons
1715 1715 16901690 1725 1725 1700 1700 1710 1710 16801680
18101810AnhydrAnhydrBandBand
18001800AcidAcid
ChlorideChloride
17601760AnhydrAnhydrBand 2Band 2
17351735EsterEster
17251725AldehydeAldehyde
17151715KetoneKetone
17101710AcidAcid
16901690AmideAmide
Factor influencing Factor influencing C=OC=O
1) conjugation1) conjugationC=CC=C
CC
OO
CC++——CCCC
OO--
Conjugation increase single bond character of Conjugation increase single bond character of C=OC=O Lower force constantLower force constant lower frequency numberlower frequency number
O
OH
Ketone and Ring StrainKetone and Ring Strain
Ring Strain: HigherRing Strain: Higher
Factors influencing Factors influencing C=OC=O
2) Ring size2) Ring size
O
1715 cm1715 cm-1-1
Angle ~ 120Angle ~ 120oo
CH3
CH3
O
O
1751 cm1751 cm-1-1
< 120< 120oo
O
1775 cm1775 cm-1-1
<< 120<< 120oo
Factors influencing carbonyl: Factors influencing carbonyl: C=OC=O
3) 3) substitution effect (Chlorine or other halogens) substitution effect (Chlorine or other halogens)
——CC——CC——
XX
OO
Result in stronger bound Result in stronger bound higher frequency higher frequency O
Cl 1750 cm1750 cm-1-1
4) Hydrogen bonding 4) Hydrogen bonding Decrease Decrease C=OC=O strenght strenghtlower frequencylower frequency
O
OCH3
OH
1680 cm1680 cm-1-1
Factors influencing carbonyl: Factors influencing carbonyl: C=OC=O5) Heteroatom5) Heteroatom
Y
R
O
Inductive effectInductive effect
Stronger bondStronger bondhigher frequencyhigher frequency
e.g. estere.g. ester
Y
R
O
Resonance effectResonance effectWeaker bondWeaker bondLower frequence Lower frequence
e.g. amidese.g. amides
YY C=OC=O
ClCl
BrBr
OH (monomer)OH (monomer)
OR (Ester)OR (Ester)
1815-17851815-1785
18121812
17601760
1705-17351705-1735
NH2NH2
SRSR
1695-16501695-1650
1720-16901720-1690
inductiveinductive
resonanceresonance
Ester CarbonylEster Carbonyl
EstersEsters C=O C=O ~ 1750 – 1735 cm~ 1750 – 1735 cm-1-1
O-C : 1300 – 1000 2 or more bandsO-C : 1300 – 1000 2 or more bands
Conjugation => lower freq.
R OR
O
Inductive effect with OInductive effect with O reinforce carbonyl => higherhigher
Conjugation withConjugation with CO CO weaken carbonyl => LowerLower
Ester carbonyl: Ester carbonyl: C=OC=O
C=O : 1765 cmC=O : 1765 cm-1-1 C-O 1215 cmC-O 1215 cm-1-1
1193 cm1193 cm-1-1
spsp22
C=OC=O
Lactone carbonyl: Lactone carbonyl: C=OC=O
Lactones Lactones Cyclic Ester Cyclic Ester
O
O
1735173517201720 17601760
1770177017501750 18001800
O
O
O
O
OO
OO O
O
Carbonyl compounds : AcidsCarbonyl compounds : Acids
Carboxylic acidCarboxylic acid
Exist as dimer :Exist as dimer :CH3 C
OH
O
CH3C
OH
O
Strong Hydrogen bondStrong Hydrogen bond
OH : Very broad OH : Very broad 3400 – 2400 cm 3400 – 2400 cm-1-1
C=O : broad C=O : broad 1730 – 1700 cm 1730 – 1700 cm-1-1
CC——O : 1320 – 1210 cmO : 1320 – 1210 cm-1-1 Medium intensity Medium intensity
Carbonyl compounds : AcidsCarbonyl compounds : Acids
C=OC=O
OHOH
C=O : 1711 cmC=O : 1711 cm-1-1
OH : Very Broad 3300 to 2500 cmOH : Very Broad 3300 to 2500 cm-1-1 C-O : 1285, 1207 cmC-O : 1285, 1207 cm-1-1
AnhydridesAnhydrides
CH3 O
O
CH3
O C=O always has 2 bands:C=O always has 2 bands:
1830-1800 and 1775-1740 cm1830-1800 and 1775-1740 cm-1-1
CC—O multiple bands 1300 – 900 cm—O multiple bands 1300 – 900 cm-1-1
Carbonyl compounds : AldehydesCarbonyl compounds : AldehydesAldehydesAldehydes C=O C=O ~ 1725 cm~ 1725 cm-1-1
O=C-H : 2 weak bands 2750, 2850 cmO=C-H : 2 weak bands 2750, 2850 cm-1-1
Conjugation => lower freq.
C=O : 1724 cmC=O : 1724 cm-1-1
Other carbonylOther carbonyl
AmidesAmides
LactamsLactams
Acid ChloridesAcid Chlorides
C=O ~1680-1630 cmC=O ~1680-1630 cm-1 -1 (band I)(band I)
NHNH22 ~ 3350 and 3180 cm ~ 3350 and 3180 cm-1-1 (stretch) (stretch)
NH ~ 3300 cmNH ~ 3300 cm-1-1 (stretch) (stretch)
NH ~ 1640-1550 cmNH ~ 1640-1550 cm-1-1 (bending) (bending)
NH
O
RR——C C —— ClCl
OO
1810-1775 cm1810-1775 cm-1-1
C C —— Cl 730 – 550 cm Cl 730 – 550 cm-1-1
~1660~1660
NH
O
~1705~1705
NH
O
~1745~1745
Increase with strainIncrease with strain
AmidesAmides
NHNH22 : Symmetrical stretch =>3170 cm : Symmetrical stretch =>3170 cm-1-1
asymmetrical stretch => 3352 cmasymmetrical stretch => 3352 cm-1-1
C=O : 1640 cmC=O : 1640 cm-1-1
NH Out of planeNH Out of plane
Amino acidAmino acid
Exist as zwitterions Exist as zwitterions
CCCOCO22
--
NHNH33++
NHNH33++ : very broad 3330-2380 : very broad 3330-2380
(OH + (OH + NHNH33++ ))
CC
OO
OO1600 – 1590 strong1600 – 1590 strong
AmineAmine
NH 3500 – 3300 cmNH 3500 – 3300 cm-1-1 NH : 2 bandsNH : 2 bandsNH : 1 bandNH : 1 band
NH bending : 1650 – 1500 cmNH bending : 1650 – 1500 cm-1-1
C-N : 1350 – 1000 cmC-N : 1350 – 1000 cm-1-1
NH out-of-plane : ~ 800 cmNH out-of-plane : ~ 800 cm-1-1
Amine saltAmine salt
NHNH++ 3500 – 3030 cm 3500 – 3030 cm-1-1 broad / strong broad / strong
Ammonium Ammonium primary primary secomdary secomdary
rightright
LeftLeft
Other Nitrogen CompoundsOther Nitrogen Compounds
NitrilesNitriles
IsocyanatesIsocyanates
IsothiocyanatesIsothiocyanates
Imines / OximesImines / Oximes
R-CR-CN : N : Sharp 2250 cmSharp 2250 cm-1-1
Conjugation moves to lower frequencyConjugation moves to lower frequency
R-N=C=OR-N=C=O Broad ~ 2270 cmBroad ~ 2270 cm-1-1
R-N=C=SR-N=C=S 2 Broad peaks ~ 2125 cm2 Broad peaks ~ 2125 cm-1-1
R R 22C=N-RC=N-R 1690 - 1640 cm1690 - 1640 cm-1-1
NitroNitro
——NNOO
OO
++--
Aliphatic :Aliphatic : Asymmetric : 1600-1530 cmAsymmetric : 1600-1530 cm-1-1
Symmetric : 1390-1300 cmSymmetric : 1390-1300 cm-1-1
Aromatic :Aromatic : Asymmetric : 1550-1490 cmAsymmetric : 1550-1490 cm-1-1
Symmetric : 1355-1315 cmSymmetric : 1355-1315 cm-1-1
SulfurSulfur
MercaptansMercaptans S – H : weak 2600-2550 cmS – H : weak 2600-2550 cm-1-1
Since only few absorption in that range it confirm its presenceSince only few absorption in that range it confirm its presence
Sulfides,Disulfides : no useful informationSulfides,Disulfides : no useful information
Sulfoxides:Sulfoxides:
RS
R
O Strong ~ 1050 cmStrong ~ 1050 cm-1-1
SulfonesSulfones:: Asymetrical ~ 1300 cmAsymetrical ~ 1300 cm-1-1
Symetrical ~ 1150 cmSymetrical ~ 1150 cm-1-1 R S R
O
O
2 bands :2 bands :
Sulfur: Sulfonyl ChlorideSulfur: Sulfonyl Chloride
S=O : S=O : Asymmetrical stretch: 1375 cm-1Asymmetrical stretch: 1375 cm-1Symmetrical Stretch : 1185 cm-1Symmetrical Stretch : 1185 cm-1
Sulfur: SulfonateSulfur: Sulfonate
S=O : S=O : Asymmetrical stretch: 1350 cm-1Asymmetrical stretch: 1350 cm-1Symmetrical Stretch : 1175 cm-1Symmetrical Stretch : 1175 cm-1
S-O : several bands between 1000 – 750 cmS-O : several bands between 1000 – 750 cm-1-1
Sulfur: SulfonamideSulfur: Sulfonamide
S=O : S=O : Asymmetrical stretch: 1325 cm-1Asymmetrical stretch: 1325 cm-1Symmetrical Stretch : 1140 cm-1Symmetrical Stretch : 1140 cm-1
NHNH22 stretch: 3350 and 3250 cm stretch: 3350 and 3250 cm-1-1 NH Bend: 1550 cmNH Bend: 1550 cm-1-1
HalogensHalogens
CC—F : 1400 – 1000 cm—F : 1400 – 1000 cm-1-1
CC—Cl : strong 785 – 540 cm—Cl : strong 785 – 540 cm-1-1
CC—Br : 650 – 510 cm—Br : 650 – 510 cm-1-1 (out of range with NaCl plates) (out of range with NaCl plates)
CC—I : 600 – 485 cm—I : 600 – 485 cm-1-1 (out of range) (out of range)
PhosphorusPhosphorus
Phosphines: R-PHPhosphines: R-PH2 2 R R22PHPH
PP—H : Sharp 2320 – 2270 cm—H : Sharp 2320 – 2270 cm-1-1
PPHH22 bending : 1090 – 1075 and 840 - 810 cm bending : 1090 – 1075 and 840 - 810 cm-1-1
PPH bending : 990 - 886 cmH bending : 990 - 886 cm-1-1
Phosphine Oxide : RPhosphine Oxide : R33 P=O P=O
PP=O very strong : 1210 - 1140 cm=O very strong : 1210 - 1140 cm-1-1
Phosphate Esters : (OR)Phosphate Esters : (OR)33 P=O P=O
PP=O very strong : 1300 - 1240 cm=O very strong : 1300 - 1240 cm-1-1
PP-O very strong : 1088 – 920 cm-O very strong : 1088 – 920 cm-1-1
PP-O : 845 - 725 cm-O : 845 - 725 cm-1-1
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