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

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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/

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Teaching SE: St udent Exercise

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Teaching SE: St udent Exercise1

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Teaching SE: St udent Exercise

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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

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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

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ACD/SE ACD/C+H NMR Predict ors

Convergence of Concept s

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Quest ions?

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Visit our hospitality suite for great games, contests, and refreshments.

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Brent G. Paulter, Ph.D.Application Scientistbrent.paulter@acdlabs.com

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