Standard Article

Lanthanide Enolates as Nuclear Magnetic Resonance Shift Reagents

Metal Enolates (2009)

  1. Thomas J. Wenzel,
  2. Katelyn A. Provencher

Published Online: 15 SEP 2010

DOI: 10.1002/9780470682531.pat0430

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Wenzel, T. J. and Provencher, K. A. 2010. Lanthanide Enolates as Nuclear Magnetic Resonance Shift Reagents. Patai's Chemistry of Functional Groups. .

Author Information

  1. Bates College, Department of Chemistry, Lewiston, Maine, USA

Publication History

  1. Published Online: 15 SEP 2010

Chemistry Terms

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Abstract

  • 1
    Introduction
  • 2
    General Considerations
  • 3
    Applications of Achiral Shift Reagents
  • 4
    Coupling of Achiral Shift Reagents to Chiral Derivatizing and Solvating Agents
  • 5
    Chiral Shift Reagents
  • 6
    Binuclear Lanthanide–Silver Shift Reagents

Keywords:

  • lanthanide enolates as nuclear magnetic resonance shift reagents;
  • achiral ligand effect;
  • applications of achiral shift reagents;
  • configurational analysis of sulfur oxide compounds;
  • coupling of achiral shift reagents - to chiral derivatizing and solvating agents;
  • chiral shift reagents;
  • assignment of absolute configuration;
  • binuclear lanthanide–silver shift reagents

Featured Compounds

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  1. 1 - 91
Compound 1
Molecular Weight:184.2753
Molecular Formula:C11H20O2
InChIKey:YRAJNWYBUCUFBD-UHFFFAOYSA-N
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Compound 2
Molecular Weight:296.182
Molecular Formula:C10H11F7O2
InChIKey:SQNZLBOJCWQLGQ-UHFFFAOYSA-N
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Compound 3
Molecular Weight:204.243
Molecular Formula:C9H18NO4
InChIKey:RDHQFKQIGNGIED-UHFFFAOYSA-O
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Compound 4
Molecular Weight:170.2487
Molecular Formula:C10H18O2
InChIKey:YMBRJMLOGNZRFY-UTINFBMNSA-N
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Compound 4'
Molecular Weight:175.227
Molecular Formula:C11H13NO
InChIKey:QKXTXXKOSUMTNX-UHFFFAOYSA-N
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Compound 4''
Molecular Weight:111.1418
Molecular Formula:C6H9NO
InChIKey:AXDBIGNYXNSBHV-UHFFFAOYSA-N
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Compound 5
Molecular Weight:217.2637
Molecular Formula:C13H15NO2
InChIKey:CPUNSUBDQUBQHZ-UHFFFAOYSA-N
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Compound 6
Molecular Weight:282.4198
Molecular Formula:C20H26O
InChIKey:LDLCBRKARDCJLI-FIWHBWSRSA-N
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Compound 7
Molecular Weight:398.5781
Molecular Formula:C26H38O3
InChIKey:UDHQRLHLHLDBHV-FMLDVPITSA-N
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Compound 8
Molecular Weight:195.3012
Molecular Formula:C12H21NO
InChIKey:VBUNAYIXLYYUIE-SOFGYWHQSA-N
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Compound 9
Molecular Weight:446.966
Molecular Formula:C13H20EuN2NiO2
InChIKey:HCVKRRNUZUAMOV-UHFFFAOYSA-L
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Compound 10
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 11
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 12
Molecular Weight:162.25
Molecular Formula:C7H14O2S
InChIKey:SAGOAKDWIVKDTC-KNVOCYPGSA-N
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Compound 13
Molecular Weight:1171.64
Molecular Formula:C34H36EuF21O9S
InChIKey:UKIXHKOEYNVAMA-BSWAEIBTSA-K
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Compound 14
Molecular Weight:174.261
Molecular Formula:C8H14O2S
InChIKey:HTEGRJFXZVNSLI-UHFFFAOYSA-N
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Compound 15
Molecular Weight:174.261
Molecular Formula:C8H14O2S
InChIKey:VGQCRPHTIKWVRB-UHFFFAOYSA-N
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Compound 16
Molecular Weight:550.7766
Molecular Formula:C36H46N4O
InChIKey:FIDRNDANECZKGX-IZOYJUGISA-N
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Compound 17
Molecular Weight:196.3291
Molecular Formula:C13H24O
InChIKey:FCXURDQZLWYZFL-UHFFFAOYSA-N
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Compound 18
Molecular Weight:140.2227
Molecular Formula:C9H16O
InChIKey:DEDZBEBBIUTZAJ-UHFFFAOYSA-N
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Compound 18'
Molecular Weight:141.2289
Molecular Formula:C9H16O
InChIKey:Not Available
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Compound 19
Molecular Weight:Not Available
Molecular Formula:(C8H8O)nC16H18O2
InChIKey:IBOWKGBARGTQCG-UHFFFAOYSA-N
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Compound 20
Molecular Weight:460.5183
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 21
Molecular Weight:850.8622
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 22
Molecular Weight:518.997
Molecular Formula:C25H34ClF3N2O4
InChIKey:TZHMOKUTVZFBHU-UHFFFAOYSA-M
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Compound 23
Molecular Weight:786.1134
Molecular Formula:C44H84NO8P
InChIKey:SNKAWJBJQDLSFF-YEUCEMRASA-N
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Compound 23'
Molecular Weight:846.2515
Molecular Formula:C48H96NO8P
InChIKey:UKDDQGWMHWQMBI-UHFFFAOYSA-N
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Compound 24
Molecular Weight:204.2649
Molecular Formula:C13H16O2
InChIKey:BVZJUBXUZBTZGD-UHFFFAOYSA-N
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Compound 24'
Molecular Weight:176.2548
Molecular Formula:C12H16O
InChIKey:KHQHVWKARBKUCT-UHFFFAOYSA-N
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Compound 25
Molecular Weight:353.3273
Molecular Formula:C15H19N3O7
InChIKey:SPVZUYZZIIOZRM-UHFFFAOYSA-N
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Compound 26
Molecular Weight:267.2464
Molecular Formula:C14H12F3NO
InChIKey:NOJXWADZEDSEGP-UHFFFAOYSA-N
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Compound 27
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 28
Molecular Weight:236.3499
Molecular Formula:C15H24O2
InChIKey:DOOCADGKJPCQSD-UHFFFAOYSA-N
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Compound 29
Molecular Weight:248.2415
Molecular Formula:C12H15F3O2
InChIKey:ISLOIHOAZDSEAJ-UHFFFAOYSA-N
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Compound 30
Molecular Weight:348.2565
Molecular Formula:C14H15F7O2
InChIKey:PEWOESYEGLBLNR-UHFFFAOYSA-N
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Compound 31
Molecular Weight:320.5093
Molecular Formula:C21H36O2
InChIKey:ZCXWUWQWHMZXOK-UHFFFAOYSA-N
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Compound 32
Molecular Weight:380.909
Molecular Formula:C12H8Cl6O
InChIKey:DFBKLUNHFCTMDC-UHFFFAOYSA-N
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Compound 32'
Molecular Weight:398.925
Molecular Formula:C12H10Cl6O2
InChIKey:NWRDBJRTQVHAKR-ARMUGHSSSA-N
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Compound 32''
Molecular Weight:398.925
Molecular Formula:C12H10Cl6O2
InChIKey:NWRDBJRTQVHAKR-JYGFWBPPSA-N
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Compound 33
Molecular Weight:122.1644
Molecular Formula:C8H10O
InChIKey:WRMNZCZEMHIOCP-UHFFFAOYSA-N
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Compound 34
Molecular Weight:105.1932
Molecular Formula:C6H14O
InChIKey:Not Available
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Compound 35
Molecular Weight:189.2646
Molecular Formula:C13H12O
InChIKey:Not Available
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Compound 36
Molecular Weight:260.194
Molecular Formula:C10H14BrNS
InChIKey:FKRDVSURONWYBY-LBEJWNQZSA-M
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Compound 37
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37a
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37b
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 37c
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 38
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 39
Molecular Weight:156.136
Molecular Formula:C7H8O4
InChIKey:DDSKZCDBPUQSPS-UHFFFAOYSA-N
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Compound 40
Molecular Weight:427.4486
Molecular Formula:C26H21NO5
InChIKey:BMVTUSNRUSZUCK-UHFFFAOYSA-N
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Compound 41
Molecular Weight:226.2689
Molecular Formula:C12H18O4
InChIKey:NIUBPGCIIPVPHK-UHFFFAOYSA-N
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Compound 42
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 43
Molecular Weight:184.0674
Molecular Formula:C7H9AsO
InChIKey:MHHKHJTUALDMPG-UHFFFAOYSA-N
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Compound 44a
Molecular Weight:416.5104
Molecular Formula:C30H24O2
InChIKey:MABZBHQYVLPDLK-UHFFFAOYSA-N
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Compound 44b
Molecular Weight:416.5104
Molecular Formula:C30H24O2
InChIKey:CAEAVANGQNZJAL-UHFFFAOYSA-N
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Compound 45
Molecular Weight:182.2179
Molecular Formula:C13H10O
InChIKey:MTIPEROSCIMKOK-TWSJNVEOSA-N
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Compound 44
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 46a
Molecular Weight:330.3319
Molecular Formula:C18H18O6
InChIKey:AWZIUZBNCBHQTI-UHFFFAOYSA-N
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Compound 46b
Molecular Weight:360.2751
Molecular Formula:C16H12N2O8
InChIKey:VWKXXMPVBIQLRJ-UHFFFAOYSA-N
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Compound 46c
Molecular Weight:302.2788
Molecular Formula:C16H14O6
InChIKey:XWHPDXLPTVOKAK-UHFFFAOYSA-N
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Compound 47
Molecular Weight:894.9994
Molecular Formula:C54H54O12
InChIKey:SQMLCHVWDQRDTG-UHFFFAOYSA-N
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Compound 48
Molecular Weight:661.0498
Molecular Formula:C42H76O5
InChIKey:HJORWPXAILIBRL-FTJRLTLYSA-N
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Compound 49
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:Not Available
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Compound 50
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:Not Available
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Compound 51
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:CRPUJAZIXJMDBK-UHFFFAOYSA-N
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Compound 52
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:GRWFGVWFFZKLTI-UHFFFAOYSA-N
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Compound 53
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:BQOFWKZOCNGFEC-UHFFFAOYSA-N
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Compound 54
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:PGBNIHXXFQBCPU-UHFFFAOYSA-N
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Compound 55
Molecular Weight:204.3511
Molecular Formula:C15H24
InChIKey:VLXDPFLIRFYIME-UHFFFAOYSA-N
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Compound 56
Molecular Weight:516.7138
Molecular Formula:C40H36
InChIKey:ZJMQXQWYDHAKIH-QYVLQNAGSA-N
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Compound 57
Molecular Weight:136.234
Molecular Formula:C10H16
InChIKey:UAHWPYUMFXYFJY-UHFFFAOYSA-N
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Compound 58
Molecular Weight:346.6327
Molecular Formula:C25H46
InChIKey:BSXYLMVBPPIDSG-WTFFSMHXSA-N
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Compound 59
Molecular Weight:158.2396
Molecular Formula:C12H14
InChIKey:GZVSTTLZDWCOIS-UHFFFAOYSA-N
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Compound 60
Molecular Weight:216.3187
Molecular Formula:C15H20O
InChIKey:VMDXHYHOJPKFEK-RZWYOFBOSA-N
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Compound 61
Molecular Weight:234.3355
Molecular Formula:C18H18
InChIKey:BUSLHLOSCTVNRQ-UHFFFAOYSA-N
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Compound 62
Molecular Weight:360.849
Molecular Formula:C7H8Br2Cl2F2
InChIKey:ZWHYQCPFCXWSOH-ZZKAVYKESA-N
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Compound 63
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:SIKJAQJRHWYJAI-UHFFFAOYSA-N
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Compound 64
Molecular Weight:67.0892
Molecular Formula:C4H5N
InChIKey:KAESVJOAVNADME-UHFFFAOYSA-N
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Compound 65
Molecular Weight:118.1326
Molecular Formula:C8H6O
InChIKey:IANQTJSKSUMEQM-UHFFFAOYSA-N
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Compound 66
Molecular Weight:182.2212
Molecular Formula:C12H10N2
InChIKey:DMLAVOWQYNRWNQ-BUHFOSPRSA-N
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Compound 67
Molecular Weight:85.128
Molecular Formula:C3H3NS
InChIKey:Not Available
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Compound 68
Molecular Weight:134.198
Molecular Formula:C8H6S
InChIKey:FCEHBMOGCRZNNI-UHFFFAOYSA-N
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Compound 69a
Molecular Weight:267.3257
Molecular Formula:C16H17N3O
InChIKey:OASFUPNFUGXVOE-ZFWWWQNUSA-N
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Compound 69b
Molecular Weight:281.3523
Molecular Formula:C17H19N3O
InChIKey:PMGMJABYWZUNPL-XEZPLFJOSA-N
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Compound 70
Molecular Weight:569.425
Molecular Formula:C29H34N4Zn2
InChIKey:XLGVAPWOPWCJSJ-ZQKGCYIASA-N
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Compound 71
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 69
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 72
Molecular Weight:304.1706
Molecular Formula:C11H17IN2
InChIKey:DYAGPCQOMOCCFX-UHFFFAOYSA-M
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Compound 73
Molecular Weight:240.069
Molecular Formula:C9H13BF4S
InChIKey:BBLYMGLIKYPOAG-UHFFFAOYSA-N
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Compound 74
Molecular Weight:568.6961
Molecular Formula:C30H48O10
InChIKey:XBYMBVDJRZHLJT-FPCALVHFSA-N
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  1. 1 - 91