Standard Article

Acidity, Basicity and H-Bonding of Double-Bonded Functional Groups: Nitrones, Nitriles and Thiocarbonyls

Double-bonded Functional Groups (1997)

  1. Claudia M. Rienäcker,
  2. Thomas M. Klapötke

Published Online: 15 DEC 2009

DOI: 10.1002/9780470682531.pat0124

Patai's Chemistry of Functional Groups

Patai's Chemistry of Functional Groups

How to Cite

Rienäcker, C. M. and Klapötke, T. M. 2009. Acidity, Basicity and H-Bonding of Double-Bonded Functional Groups: Nitrones, Nitriles and Thiocarbonyls. Patai's Chemistry of Functional Groups. .

Author Information

  1. University of Glasgow, Department of Chemistry, Glasgow, UK

  1. Author to whom correspondence should be addressed

Publication History

  1. Published Online: 15 DEC 2009

Abstract

  • 1
    Introduction
  • 2
    Acid-Base Reactions
  • 3
    Nitrones
  • 4
    Nitriles
  • 5
    Thiocarbonyls
  • 6
    Acknowledgements

Keywords:

  • acidity and basicity of hydrogen bonding of organic compounds;
  • acid base reactions;
  • gas-phase proton affinities;
  • possible formation mechanism;
  • Schmidt reaction - carbonyl group transformation into nitriles;
  • hydrogen-bond cyanamide basicity;
  • proton affinities of nitriles;
  • gas-phase basicity and proton affinity

Featured Compounds

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  1. 1 - 61
Compound 1a
Molecular Weight:161.2435
Molecular Formula:C11H15N
InChIKey:KFLSWDVYGSSZRX-FMIVXFBMSA-N
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Compound 1b
Molecular Weight:181.2331
Molecular Formula:C13H11N
InChIKey:UVEWQKMPXAHFST-SDNWHVSQSA-N
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Compound 1c
Molecular Weight:206.2411
Molecular Formula:C11H14N2O2
InChIKey:BZCRPTQYJYKZDH-XYOKQWHBSA-N
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Compound 1d
Molecular Weight:191.2695
Molecular Formula:C12H17NO
InChIKey:MPYQZDRGFVCQBT-UKTHLTGXSA-N
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Compound 1e
Molecular Weight:127.2273
Molecular Formula:C8H17N
InChIKey:KLUWMRAQLXQISC-RMKNXTFCSA-N
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Compound 1f
Molecular Weight:161.2435
Molecular Formula:C11H15N
InChIKey:QPMNQRGLWJEIAB-FMIVXFBMSA-N
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Compound 2a
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:IYSYLWYGCWTJSG-FMIVXFBMSA-N
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Compound 3d
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:RSBGOXJMPUJSCP-UHFFFAOYSA-N
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Compound 4a
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:HYWWTHOGCJXTRI-UHFFFAOYSA-N
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Compound 4b
Molecular Weight:197.2325
Molecular Formula:C13H11NO
InChIKey:ZVSKZLHKADLHSD-UHFFFAOYSA-N
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Compound 4c
Molecular Weight:222.2405
Molecular Formula:C11H14N2O3
InChIKey:FHLKNAGHERYTJV-UHFFFAOYSA-N
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Compound 4d
Molecular Weight:207.2689
Molecular Formula:C12H17NO2
InChIKey:JZHSACJKCPNPHW-UHFFFAOYSA-N
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Compound 4e
Molecular Weight:143.2267
Molecular Formula:C8H17NO
InChIKey:OEIZGTXQZLSLFL-UHFFFAOYSA-N
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Compound 3a
Molecular Weight:177.2429
Molecular Formula:C11H15NO
InChIKey:YFBUTSZDUOMTAP-UHFFFAOYSA-N
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Compound 9
Molecular Weight:83.1317
Molecular Formula:C5H9N
InChIKey:RFFFKMOABOFIDF-UHFFFAOYSA-N
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Compound I
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound II
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 7
Molecular Weight:69.1051
Molecular Formula:C4H7N
InChIKey:Not Available
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Compound 8
Molecular Weight:69.1051
Molecular Formula:C4H7N
InChIKey:Not Available
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Compound 10
Molecular Weight:83.1317
Molecular Formula:C5H9N
InChIKey:JAMNHZBIQDNHMM-UHFFFAOYSA-N
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Compound 11
Molecular Weight:87.143
Molecular Formula:C3H5NS
InChIKey:ZRIGDBVSVFSVLL-UHFFFAOYSA-N
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Compound 12
Molecular Weight:101.17
Molecular Formula:C4H7NS
InChIKey:VWWGZUJJFSTWTN-UHFFFAOYSA-N
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Compound 13
Molecular Weight:115.197
Molecular Formula:C5H9NS
InChIKey:VVOIVFPLDQYDNZ-UHFFFAOYSA-N
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Compound 14
Molecular Weight:71.0779
Molecular Formula:C3H5NO
InChIKey:QKPVEISEHYYHRH-UHFFFAOYSA-N
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Compound 15
Molecular Weight:89.524
Molecular Formula:C3H4ClN
InChIKey:GNHMRTZZNHZDDM-UHFFFAOYSA-N
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Compound 16
Molecular Weight:117.1479
Molecular Formula:C8H7N
InChIKey:SUSQOBVLVYHIEX-UHFFFAOYSA-N
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Compound 17
Molecular Weight:193.2438
Molecular Formula:C14H11N
InChIKey:NEBPTMCRLHKPOB-UHFFFAOYSA-N
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Compound 18
Molecular Weight:269.3398
Molecular Formula:C20H15N
InChIKey:DFXWCQCJIMWRNI-UHFFFAOYSA-N
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Compound 19
Molecular Weight:162.1454
Molecular Formula:C8H6N2O2
InChIKey:Not Available
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Compound 21
Molecular Weight:113.1146
Molecular Formula:C5H7NO2
InChIKey:ZIUSEGSNTOUIPT-UHFFFAOYSA-N
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Compound 22
Molecular Weight:66.0614
Molecular Formula:C3H2N2
InChIKey:Not Available
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Compound 33
Molecular Weight:76.121
Molecular Formula:CH4N2S
InChIKey:UMGDCJDMYOKAJW-UHFFFAOYSA-N
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Compound 24
Molecular Weight:60.118
Molecular Formula:C2H4S
InChIKey:QJFUMFCCMJJLIE-UHFFFAOYSA-N
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Compound 32
Molecular Weight:74.145
Molecular Formula:C3H6S
InChIKey:JTNXQVCPQMQLHK-UHFFFAOYSA-N
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Compound Ia
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound Ib
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound IIa
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound IIb
Molecular Weight:Not Available
Molecular Formula:Not Available
InChIKey:Not Available
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Compound 30
Molecular Weight:89.159
Molecular Formula:C3H7NS
InChIKey:SKECXRFZFFAANN-UHFFFAOYSA-N
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Compound 36
Molecular Weight:114.982
Molecular Formula:CCl2S
InChIKey:ZWZVWGITAAIFPS-UHFFFAOYSA-N
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Compound 37
Molecular Weight:75.133
Molecular Formula:C2H5NS
InChIKey:YUKQRDCYNOVPGJ-UHFFFAOYSA-N
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Compound 41
Molecular Weight:103.186
Molecular Formula:C4H9NS
InChIKey:LKNQXZAHNDFIQY-UHFFFAOYSA-N
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Compound 43
Molecular Weight:104.171
Molecular Formula:C4H8OS
InChIKey:IEPFHYMMMGMRNF-UHFFFAOYSA-N
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Compound 45
Molecular Weight:104.174
Molecular Formula:C3H8N2S
InChIKey:VLCDUOXHFNUCKK-UHFFFAOYSA-N
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Compound 47
Molecular Weight:122.209
Molecular Formula:C3H6OS2
InChIKey:LABVNFAVENLDHB-UHFFFAOYSA-N
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Compound 48
Molecular Weight:119.185
Molecular Formula:C4H9NOS
InChIKey:QPKDBLGFWZSDSB-UHFFFAOYSA-N
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Compound 49
Molecular Weight:132.227
Molecular Formula:C5H12N2S
InChIKey:MNOILHPDHOHILI-UHFFFAOYSA-N
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Compound 50
Molecular Weight:158.304
Molecular Formula:C9H18S
InChIKey:HMMKPVYDAVOBLX-UHFFFAOYSA-N
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Compound 35
Molecular Weight:82.073
Molecular Formula:CF2S
InChIKey:FOCAHLGSDWHSAH-UHFFFAOYSA-N
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Compound 25
Molecular Weight:61.106
Molecular Formula:CH3NS
InChIKey:CYEBJEDOHLIWNP-UHFFFAOYSA-N
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Compound 26
Molecular Weight:62.091
Molecular Formula:CH2OS
InChIKey:AWIJRPNMLHPLNC-UHFFFAOYSA-N
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Compound 27
Molecular Weight:64.082
Molecular Formula:CHFS
InChIKey:OSVFSRQDGXDPRD-UHFFFAOYSA-N
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Compound 28
Molecular Weight:80.537
Molecular Formula:CHClS
InChIKey:KTBJFVJBDRTXMD-UHFFFAOYSA-N
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Compound 29
Molecular Weight:74.145
Molecular Formula:C3H6S
InChIKey:UXBLKIPIXRLLBH-UHFFFAOYSA-N
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Compound 31
Molecular Weight:76.118
Molecular Formula:C2H4OS
InChIKey:NOGORYGYLODPPL-UHFFFAOYSA-N
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Compound 34
Molecular Weight:78.09
Molecular Formula:CH2O2S
InChIKey:HDFRDWFLWVCOGP-UHFFFAOYSA-N
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Compound 38
Molecular Weight:76.118
Molecular Formula:C2H4OS
InChIKey:DUYAAUVXQSMXQP-UHFFFAOYSA-N
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Compound 39
Molecular Weight:78.109
Molecular Formula:C2H3FS
InChIKey:YSGVZLDVFLDBEM-UHFFFAOYSA-N
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Compound 40
Molecular Weight:94.563
Molecular Formula:C2H3ClS
InChIKey:MXZBXCKWSHEHAP-UHFFFAOYSA-N
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Compound 42
Molecular Weight:90.144
Molecular Formula:C3H6OS
InChIKey:DTOZRCOCJVVION-UHFFFAOYSA-N
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Compound 44
Molecular Weight:104.171
Molecular Formula:C4H8OS
InChIKey:RVEBJDGWKWKYBH-UHFFFAOYSA-N
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  1. 1 - 61