acd/labs goes back to school · carbon hybridization sp3 sp not sp = sp2 or sp3 c not defined sp2...
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ACD/Labs Goes Back t o School:NMR Chem ical Shif t Predict ion t o
St ruct ure Elucidat ionBrent Pautler Ph.D, Application Scientist
ACD/Labs User Meeting ENC 2017
For t he Love of NMR!
#1 NMR Chem ical Shif t Predict ion
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NMR Chem ical Shif t Predict ion Exercise
NMR Chem ical Shif t Calculat ions
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𝐻𝐻𝑁𝑁𝑁𝑁𝑁𝑁Ψ = 𝐸𝐸Ψ
𝐸𝐸 = ℎν0 = ℎ𝛾𝛾𝐵𝐵02𝜋𝜋
ν = 𝛾𝛾𝐵𝐵02𝜋𝜋
1 − 𝜎𝜎𝛿𝛿 = 𝜎𝜎𝑟𝑟𝑟𝑟𝑟𝑟 − 𝜎𝜎𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑠𝑟𝑟
𝜎𝜎 =𝜎𝜎𝑥𝑥𝑥𝑥 0 00 𝜎𝜎𝑦𝑦𝑦𝑦 00 0 𝜎𝜎𝑧𝑧𝑧𝑧
1st Pr inciples
Em pir ical
Ab Init io NMR Calculat ions
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• Gauge-Including At om ic Orbit al Met hod (GIAO)– Quantum-mechanical results which do not depend on the
magnetic vector of the molecule
NMR Predict ors
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Hierarchical Organisation of Spherical Environments (HOSE)
Artificial Neural Network (ANN)
The Exercise
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Hartree-Fock (HF)Density Functional Theory (DFT)Second order Møllrt-Plesset perturbation theory (MP2)
C+H NMR Predictors
Expect ed Result s
9
NMR Shielding Tensor Visualization
Chemical Shift Comparison
HF DFT ACD C+H
#2 St ruct ure Elucidat ion by NMR
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114/11/2017
St ruct ure Elucidat ion Tut or ial Sof t ware
http://www.acdlabs.com/resources/freeware/teaching_se/
124/11/2017
Teaching SE: St udent Exercise
134/11/2017
Teaching SE: St udent Exercise1
2
3
144/11/2017
Teaching SE: St udent Exercise
154/11/2017
Teaching SE: St udent Exercise
CHCH2
C
C
CHC
Carbon Hybridization
sp3
sp
not sp = sp2 or sp3
C
not defined
sp2
CH
CH30 CH3
0CH2
CH2
CCH
CH30
CH2
CH
H
sp3 spsp2C C C
O O
N+ N N
N N
Atom Type Total Possibility
3
1
5
2
OO
CH2(22.90)(1.97) CH2
(29.70)(2.78)
CH2(38.40)(2.46)
CH3(54.90)(3.72)
CH(112.10)(6.56)
CH(112.60)(6.68)
C125.80 CH
(129.00)(7.86)
C145.40
C163.10
C196.40
164/11/2017
Teaching SE: St udent Exercise
CHCH2
C
C
CHC
Carbon Hybridization
sp3
sp
not sp = sp2 or sp3
C
not defined
sp2
CH
CH30 CH3
0CH2
CH2
CCH
CH30
CH2
CH
C C C
H
C
CH C C C
C C
H H
C
H
CH CH CH
NMR:
1H-13C HMBC 1H-1H COSY
MCD:
1JCC = 3JHH1JCC = 2JHC
3JCC = 4JHC2JCC = 4JHH
2JHC
4JHC
4JHH3JHH
C1
C2
1JCC = 3JHHC1
C2
1-2JCC = 2-3JHCC1
C2
1-3JCC = 2-4JHC
= 3 combo = 9 combo = 22 combo
Convergence of Concept s
4/11/2017 Advanced Chemistry Development, Inc. (ACD/Labs) 17
ACD/SE ACD/C+H NMR Predict ors
Convergence of Concept s
4/11/2017 Advanced Chemistry Development, Inc. (ACD/Labs) 18
Quest ions?
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Brent G. Paulter, Ph.D.Application [email protected]
Advanced Chemistry Development, Inc.8 King Street East, Suite 107Toronto, Ontario, Canada M5C 1B5Tel: 416-368-3435 x300Toll Free: 1-800-304-3988www.acdlabs.com