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Twistane

May 02, 2024

Twistane (IUPAC name: tricyclo[4.4.0.03,8]decane[2]) is an organic compound with the formula C10H16.[3] It is a cycloalkane and an isomer of the simplest diamondoid, adamantane, and like adamantane, is not very volatile. Twistane was named for the way its rings are permanently forced into the cyclohexane conformation known as the "twist-boat".[1] The compound was first reported by Whitlock in 1962.[4]

Twistane
Names
Preferred IUPAC name
Tricyclo[4.4.0.03,8]decane
Identifiers
  • 253-14-5 Y
  • (−): 37165-27-8 N
  • (+): 21449-14-9 N
3D model (JSmol)
  • Interactive image
1919499; 2232311
ChEBI
  • CHEBI:32904 N
ChemSpider
  • 4574225
  • (−): 34984822
  • (+): 34984821
  • 5460768
UNII
  • 4T296B0U5O Y
  • DTXSID20420120
  • InChI=1/C10H16/c1-2-8-6-9-3-4-10(8)5-7(1)9/h7-10H,1-6H2
  • C1CC2CC3CCC2CC13
Properties
C10H16
Molar mass 136.238 g·mol−1
Melting point 163 to 164.8 °C (325.4 to 328.6 °F; 436.1 to 437.9 K)[1]
Structure
D2
0 D
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YN ?)

Synthesis edit

Twistane has been synthesized in a variety of ways. The original 1962 method was based on a bicyclo[2.2.2]octane framework.[4] A 1967 publication concerned an intramolecular aldol condensation of a cis-decalin diketone.[5] It is formed when basketane is hydrogenated.[6] [dubious – discuss]

Symmetry edit

The only symmetry operation in twistane is rotation, and there exist three 2-fold axes as shown in the left picture. Thus the point group of twistane is D2. Although twistane has four stereocenters, it only exists as two enantiomers. This is because it is symmetric along its C2 axis.[7]

Polytwistane edit

Polytwistane is a hypothetical polymer of fused twistane units awaiting actual synthesis.[8][9][10][11]

References edit

  1. ^ a b Beyer, Hans; Walter, Wolfgang; trans. Douglas Lloyd (1997), Organic Chemistry, Horwood Publishing, p. 416, ISBN 1-898563-37-3, retrieved 2008-12-09
  2. ^ Quinkert, Gerhard; Egert, Ernst; Griesinger, Christian; trans. Andrew Beard (1996), Aspects of Organic Chemistry: Structure, Basel, Switzerland: Helvetica Chimica Acta, p. 107, ISBN 3-906390-15-2, retrieved 2008-12-09
  3. ^ Classics in Hydrocarbon Chemistry: Syntheses, Concepts, Perspectives Henning Hopf ISBN 978-3-527-29606-4. 2000
  4. ^ a b Tricyclo[4.4.0.03.8]Decane H. W. Whitlock Journal of the American Chemical Society 1962 84 (17), 3412-3413 doi:10.1021/ja00876a047
  5. ^ A new synthesis of twistane Jean Gauthier, Pierre Deslongchamps Canadian Journal of Chemistry, 1967, 45(3): 297-300, doi:10.1139/v67-052
  6. ^ Ho, Tse-Lok (1995), Symmetry: A Basis for Synthesis Design, Wiley-IEEE, p. 69, ISBN 0-471-57376-0, retrieved 2008-12-10
  7. ^ Kalsi, P. S. (2005), Stereochemistry Conformation and Mechanism, New Age Publishers, p. 94, ISBN 81-224-1564-4, retrieved 2008-12-10
  8. ^ Barua, S. R., Quanz, H., Olbrich, M., Schreiner, P. R., Trauner, D. and Allen, W. D. (2014), Polytwistane. Chem. Eur. J., 20: 1638–1645. doi:10.1002/chem.201303081
  9. ^ A step toward polytwistane: synthesis and characterization of C2-symmetric tritwistane Martin Olbrich, Peter Mayer and Dirk Trauner Org. Biomol. Chem., 2014,12, 108-112 doi:10.1039/C3OB42152J
  10. ^ Synthetic Studies toward Polytwistane Hydrocarbon Nanorods Martin Olbrich, Peter Mayer, and Dirk Trauner The Journal of Organic Chemistry Article ASAP 2014 doi:10.1021/jo502618g
  11. ^ Calculated Nuclear Magnetic Resonance Spectra of Polytwistane and Related Hydrocarbon Nanorods Boris Maryasin, Martin Olbrich, Dirk Trauner and Christian Ochsenfeld J. Chem. Theory Comput., 2015,11(3), 1020-1026 doi:10.1021/ct5011505

May 02, 2024
twistane, iupac, name, tricyclo, decane, organic, compound, with, formula, c10h16, cycloalkane, isomer, simplest, diamondoid, adamantane, like, adamantane, very, volatile, named, rings, permanently, forced, into, cyclohexane, conformation, known, twist, boat, . Twistane IUPAC name tricyclo 4 4 0 03 8 decane 2 is an organic compound with the formula C10H16 3 It is a cycloalkane and an isomer of the simplest diamondoid adamantane and like adamantane is not very volatile Twistane was named for the way its rings are permanently forced into the cyclohexane conformation known as the twist boat 1 The compound was first reported by Whitlock in 1962 4 Twistane Names Preferred IUPAC name Tricyclo 4 4 0 03 8 decane Identifiers CAS Number 253 14 5 Y 37165 27 8 N 21449 14 9 N 3D model JSmol Interactive image Beilstein Reference 1919499 2232311 ChEBI CHEBI 32904 N ChemSpider 4574225 34984822 34984821 PubChem CID 5460768 UNII 4T296B0U5O Y CompTox Dashboard EPA DTXSID20420120 InChI InChI 1 C10H16 c1 2 8 6 9 3 4 10 8 5 7 1 9 h7 10H 1 6H2 SMILES C1CC2CC3CCC2CC13 Properties Chemical formula C 10H 16 Molar mass 136 238 g mol 1 Melting point 163 to 164 8 C 325 4 to 328 6 F 436 1 to 437 9 K 1 Structure Coordination geometry D2 Dipole moment 0 D Except where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa N verify what is Y N Infobox references Contents 1 Synthesis 2 Symmetry 3 Polytwistane 4 ReferencesSynthesis editTwistane has been synthesized in a variety of ways The original 1962 method was based on a bicyclo 2 2 2 octane framework 4 A 1967 publication concerned an intramolecular aldol condensation of a cis decalin diketone 5 It is formed when basketane is hydrogenated 6 dubious discuss Symmetry editThe only symmetry operation in twistane is rotation and there exist three 2 fold axes as shown in the left picture Thus the point group of twistane is D2 Although twistane has four stereocenters it only exists as two enantiomers This is because it is symmetric along its C2 axis 7 Polytwistane editPolytwistane is a hypothetical polymer of fused twistane units awaiting actual synthesis 8 9 10 11 References edit a b Beyer Hans Walter Wolfgang trans Douglas Lloyd 1997 Organic Chemistry Horwood Publishing p 416 ISBN 1 898563 37 3 retrieved 2008 12 09 Quinkert Gerhard Egert Ernst Griesinger Christian trans Andrew Beard 1996 Aspects of Organic Chemistry Structure Basel Switzerland Helvetica Chimica Acta p 107 ISBN 3 906390 15 2 retrieved 2008 12 09 Classics in Hydrocarbon Chemistry Syntheses Concepts Perspectives Henning Hopf ISBN 978 3 527 29606 4 2000 a b Tricyclo 4 4 0 03 8 Decane H W Whitlock Journal of the American Chemical Society 1962 84 17 3412 3413 doi 10 1021 ja00876a047 A new synthesis of twistane Jean Gauthier Pierre Deslongchamps Canadian Journal of Chemistry 1967 45 3 297 300 doi 10 1139 v67 052 Ho Tse Lok 1995 Symmetry A Basis for Synthesis Design Wiley IEEE p 69 ISBN 0 471 57376 0 retrieved 2008 12 10 Kalsi P S 2005 Stereochemistry Conformation and Mechanism New Age Publishers p 94 ISBN 81 224 1564 4 retrieved 2008 12 10 Barua S R Quanz H Olbrich M Schreiner P R Trauner D and Allen W D 2014 Polytwistane Chem Eur J 20 1638 1645 doi 10 1002 chem 201303081 A step toward polytwistane synthesis and characterization of C2 symmetric tritwistane Martin Olbrich Peter Mayer and Dirk Trauner Org Biomol Chem 2014 12 108 112 doi 10 1039 C3OB42152J Synthetic Studies toward Polytwistane Hydrocarbon Nanorods Martin Olbrich Peter Mayer and Dirk Trauner The Journal of Organic Chemistry Article ASAP 2014 doi 10 1021 jo502618g Calculated Nuclear Magnetic Resonance Spectra of Polytwistane and Related Hydrocarbon Nanorods Boris Maryasin Martin Olbrich Dirk Trauner and Christian Ochsenfeld J Chem Theory Comput 2015 11 3 1020 1026 doi 10 1021 ct5011505 Retrieved from https en wikipedia org w index php title Twistane amp oldid 1211373659, wikipedia, wiki, book, books, library,

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