ACS Publications. Most Trusted. Most Cited. Most Read
Reactivity of [1(2,3)4]Pentamantane (Td-Pentamantane): A Nanoscale Model of Diamond

OR SEARCH CITATIONS

My Activity
Publications

Figure 1Loading Img
Download Hi-Res ImageDownload to MS-PowerPointCite This:J. Org. Chem. 2006, 71, 22, 8532-8540
    Article

    Reactivity of [1(2,3)4]Pentamantane (Td-Pentamantane): A Nanoscale Model of Diamond†
    Click to copy article linkArticle link copied!

    • Andrey A. Fokin*
      Andrey A. Fokin
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.
      Email: [email protected]
      More by Andrey A. Fokin
    • Peter R. Schreiner*
      Peter R. Schreiner
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.
      Email: [email protected]
      More by Peter R. Schreiner
    • Natalie A. Fokina
      Natalie A. Fokina
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      Email: [email protected]
      More by Natalie A. Fokina
    • Boryslav A. Tkachenko
      Boryslav A. Tkachenko
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      Email: [email protected]
      More by Boryslav A. Tkachenko
    • Heike Hausmann
      Heike Hausmann
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      Email: [email protected]
      More by Heike Hausmann
    • Michael Serafin
      Michael Serafin
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      Email: [email protected]
      More by Michael Serafin
    • Jeremy E. P. Dahl
      Jeremy E. P. Dahl
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      Email: [email protected]
      More by Jeremy E. P. Dahl
    • Shenggao Liu
      Shenggao Liu
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      Email: [email protected]
      More by Shenggao Liu
    • Robert M. K. Carlson
      Robert M. K. Carlson
      Institut für Organische Chemie and Institut für Anorganische und Analytische Chemie, Justus-Liebig University, Heinrich-Buff-Ring 58, D-35392 Giessen, Germany, Department of Organic Chemistry, Kiev Polytechnic Institute, pr. Pobedy 37, 03056 Kiev, Ukraine, and MolecularDiamond Technologies, Chevron Technology Ventures, 100 Chevron Way, Richmond, California 94802
      Email: [email protected]
      More by Robert M. K. Carlson
    Other Access OptionsSupporting Information (4)

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2006, 71, 22, 8532–8540
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo061561x
    Published September 26, 2006
    Copyright © 2006 American Chemical Society
    Request reuse permissions

    Abstract

    Click to copy section linkSection link copied!
    Abstract Image

    To model the chemical properties of the hydrogen-terminated nanodiamond {111} and {110} surfaces, the functionalizations of the higher diamondoid [1(2,3)4]pentamantane were studied. [1(2,3)4]Pentamantane reacts selectively with neat bromine to give the medial 2-mono- and 2,4-disubstitution products. In contrast, oxidation with nitric acid as well as single-electron-transfer oxidation involving the [1(2,3)4]pentamantane radical cation results in apical C7-substitutions. This substitution pattern dominates in the free-radical bromination under phase-transfer catalytic conditions that gives a mixture of 7- and 2-bromo[1(2,3)4]pentamantane in a 95:5 ratio. Replacement of the functional groups in [1(2,3)4]pentamantane occurs without isomerization. This was demonstrated for the interconversions of the bromo and hydroxy derivatives as well as for the preparation of [1(2,3)4]pentamantyl-7-thiol from 7-hydroxy[1(2,3)4]pentamantane. Thus, the selective functionalization of hydrogen-terminated nanodiamonds is possible by means of reactions with common electrophiles−oxidizers.

    Copyright © 2006 American Chemical Society

    Subjects

    what are subjects

    Read this article

    To access this article, please review the available access options below.

    Get instant access

    Purchase Access

    Read this article for 48 hours. Check out below using your ACS ID or as a guest.

    Recommended

    Access through Your Institution

    You may have access to this article through your institution.

    Your institution does not have access to this content. Add or change your institution or let them know you’d like them to include access.

    Supporting Information

    Click to copy section linkSection link copied!

    Absolute energies and xyz-coordinates of all computed species and 13C NMR spectra of all [1(2,3)4]pentamantane derivatives. This material is available free of charge via the Internet at http://pubs.acs.org.

    Terms & Conditions

    Most electronic Supporting Information files are available without a subscription to ACS Web Editions. Such files may be downloaded by article for research use (if there is a public use license linked to the relevant article, that license may permit other uses). Permission may be obtained from ACS for other uses through requests via the RightsLink permission system: http://pubs.acs.org/page/copyright/permissions.html.

    Cited By

    Click to copy section linkSection link copied!
    Citation Statements
    Explore this article's citation statements on scite.ai
    powered by  Scite

    This article is cited by 58 publications.

    1. Aidan W. McFord, Craig P. Butts, Natalie Fey, Roger W. Alder. 3× Axial vs 3× Equatorial: The ΔGGA Value Is a Robust Computational Measure of Substituent Steric Effects. Journal of the American Chemical Society 2021, 143 (34) , 13573-13578. https://doi.org/10.1021/jacs.1c04247
    2. Ella M. King, Matthew A. Gebbie, Nicholas A. Melosh. Impact of Rigidity on Molecular Self-Assembly. Langmuir 2019, 35 (48) , 16062-16069. https://doi.org/10.1021/acs.langmuir.9b01824
    3. Andrey A. Fokin, Raisa I. Yurchenko, Boryslav A. Tkachenko, Natalie A. Fokina, Maria A. Gunawan, Didier Poinsot, Jeremy E. P. Dahl, Robert M. K. Carlson, Michael Serafin, Hélène Cattey, Jean-Cyrille Hierso, and Peter R. Schreiner . Selective Preparation of Diamondoid Phosphonates. The Journal of Organic Chemistry 2014, 79 (11) , 5369-5373. https://doi.org/10.1021/jo500793m
    4. Ming-Hua Hsu, Hong Chuang, Fong-Yu Cheng, Ying-Pei Huang, Chien-Chung Han, Jiun-Yu Chen, Su-Chin Huang, Jen-Kun Chen, Dian-Syue Wu, Hsueh-Liang Chu, and Chia-Ching Chang . Directly Thiolated Modification onto the Surface of Detonation Nanodiamonds. ACS Applied Materials & Interfaces 2014, 6 (10) , 7198-7203. https://doi.org/10.1021/am500324z
    5. Andrey A. Fokin, Tatyana S. Zhuk, Alexander E. Pashenko, Valeriy V. Osipov, Pavel A. Gunchenko, Michael Serafin, and Peter R. Schreiner . Functionalization of Homodiamantane: Oxygen Insertion Reactions without Rearrangement with Dimethyldioxirane. The Journal of Organic Chemistry 2014, 79 (4) , 1861-1866. https://doi.org/10.1021/jo4026594
    6. Andrey A. Fokin, Lesya V. Chernish, Pavel A. Gunchenko, Evgeniya Yu. Tikhonchuk, Heike Hausmann, Michael Serafin, Jeremy E. P. Dahl, Robert M. K. Carlson, and Peter R. Schreiner . Stable Alkanes Containing Very Long Carbon–Carbon Bonds. Journal of the American Chemical Society 2012, 134 (33) , 13641-13650. https://doi.org/10.1021/ja302258q
    7. Peter R. Schreiner, Andrey A. Fokin, Hans Peter Reisenauer, Boryslav A. Tkachenko, Elemér Vass, Marilyn M. Olmstead, Dieter Bläser, Roland Boese, Jeremy E. P. Dahl and Robert M. K. Carlson . [123]Tetramantane: Parent of a New Family of σ-Helicenes. Journal of the American Chemical Society 2009, 131 (32) , 11292-11293. https://doi.org/10.1021/ja904527g
    8. Andrey A. Fokin, Tatyana S. Zhuk, Alexander E. Pashenko, Pavlo O. Dral, Pavel A. Gunchenko, Jeremy E. P. Dahl, Robert M. K. Carlson, Tatyana V. Koso, Michael Serafin and Peter R. Schreiner . Oxygen-Doped Nanodiamonds: Synthesis and Functionalizations. Organic Letters 2009, 11 (14) , 3068-3071. https://doi.org/10.1021/ol901089h
    9. Hartmut Schwertfeger, Christian Würtele, Michael Serafin, Heike Hausmann, Robert M. K. Carlson, Jeremy E. P. Dahl and Peter R. Schreiner . Monoprotection of Diols as a Key Step for the Selective Synthesis of Unequally Disubstituted Diamondoids (Nanodiamonds). The Journal of Organic Chemistry 2008, 73 (19) , 7789-7792. https://doi.org/10.1021/jo801321s
    10. Trevor M. Willey, Jason D. Fabbri, Jonathan R. I. Lee, Peter R. Schreiner, Andrey A. Fokin, Boryslav A. Tkachenko, Nataliya A. Fokina, Jeremy E. P. Dahl, Robert M. K. Carlson, Andrew L. Vance, Wanli Yang, Louis J. Terminello, Tony van Buuren and Nicolas A. Melosh . Near-Edge X-ray Absorption Fine Structure Spectroscopy of Diamondoid Thiol Monolayers on Gold. Journal of the American Chemical Society 2008, 130 (32) , 10536-10544. https://doi.org/10.1021/ja711131e
    11. Andrey A. Fokin,, Ekaterina D. Butova,, Lesya V. Chernish,, Natalie A. Fokina,, Jeremy E. P. Dahl,, Robert M. K. Carlson, and, Peter R. Schreiner. Simple Preparation of Diamondoid 1,3-Dienes via Oxetane Ring Opening. Organic Letters 2007, 9 (13) , 2541-2544. https://doi.org/10.1021/ol070920n
    12. E. A. Shokova, J. K. Kim, V. V. Kovalev. Adamantane: On the 90th Anniversary of Its Appearance in Chemical Science. Russian Journal of Organic Chemistry 2024, 60 (10) , 1831-1891. https://doi.org/10.1134/S1070428024100014
    13. . Diamondoids as Alkane CH Activation Models. 2024, 63-74. https://doi.org/10.1002/9783527812950.ch3
    14. . Preparative Diamondoid Functionalizations. 2024, 75-136. https://doi.org/10.1002/9783527812950.ch4
    15. . Diamondoid Self‐Assembly. 2024, 137-169. https://doi.org/10.1002/9783527812950.ch5
    16. Yoshifumi Toyama, Takaku Yoshihara, Hiroki Shudo, Hideto Ito, Kenichiro Itami, Akiko Yagi. Synthesis of diamondoids through hydrogenation of adamantane-annulated arenes. Chemistry Letters 2024, 53 (1) https://doi.org/10.1093/chemle/upad037
    17. Jeroen Prooth, Michael Petrov, Alevtina Shmakova, Michal Gulka, Petr Cigler, Jan D'Haen, Hans‐Gerd Boyen, Milos Nesladek. Long Spin Relaxation Times in CVD‐Grown Nanodiamonds. Advanced Quantum Technologies 2023, 6 (12) https://doi.org/10.1002/qute.202300004
    18. Stela Dragomanova, Velichka Andonova. Adamantane-containing drug delivery systems. Pharmacia 2023, 70 (4) , 1057-1066. https://doi.org/10.3897/pharmacia.70.e111593
    19. William K. Weigel, Hoang T. Dang, Abigail Feceu, David B. C. Martin. Direct radical functionalization methods to access substituted adamantanes and diamondoids. Organic & Biomolecular Chemistry 2021, 20 (1) , 10-36. https://doi.org/10.1039/D1OB01916C
    20. A. I. Nekhaev, A. L. Maksimov. Diamondoids in Oil and Gas Condensates (Review). Petroleum Chemistry 2019, 59 (10) , 1108-1117. https://doi.org/10.1134/S0965544119100098
    21. E. I. Bagrii, A. I. Nekhaev, A. L. Maksimov. Oxidative functionalization of adamantanes (review). Petroleum Chemistry 2017, 57 (3) , 183-197. https://doi.org/10.1134/S0965544117020128
    22. Marta Larrosa, Sven Heiles, Jonathan Becker, Bernhard Spengler, Radim Hrdina. CH Bond Arylation of Diamondoids Catalyzed by Palladium(II) Acetate. Advanced Synthesis & Catalysis 2016, 358 (13) , 2163-2171. https://doi.org/10.1002/adsc.201600156
    23. Sherif Abdulkader Tawfik, X. Y. Cui, S. P. Ringer, C. Stampfl. Enhanced oscillatory rectification and negative differential resistance in pentamantane diamondoid–cumulene systems. Nanoscale 2016, 8 (6) , 3461-3466. https://doi.org/10.1039/C5NR07467C
    24. J. Iskra. 35.2.1.1.8 Synthesis by Substitution of Hydrogen (Update 2015). 2016https://doi.org/10.1055/sos-SD-135-00077
    25. Radim Hrdina, Fabian M. Metz, Marta Larrosa, Jan‐Philipp Berndt, Yevgeniya Y. Zhygadlo, Sabine Becker, Jonathan Becker. Intramolecular C–H Amination Reaction Provides Direct Access to 1,2‐Disubstituted Diamondoids. European Journal of Organic Chemistry 2015, 2015 (28) , 6231-6236. https://doi.org/10.1002/ejoc.201500691
    26. Yingjie Zhou, Alex D. Brittain, Deyuan Kong, Min Xiao, Yuezhong Meng, Luyi Sun. Derivatization of diamondoids for functional applications. Journal of Materials Chemistry C 2015, 3 (27) , 6947-6961. https://doi.org/10.1039/C5TC01377A
    27. W A Clay, J E P Dahl, R M K Carlson, N A Melosh, Z-X Shen. Physical properties of materials derived from diamondoid molecules. Reports on Progress in Physics 2015, 78 (1) , 016501. https://doi.org/10.1088/0034-4885/78/1/016501
    28. Maria A. Gunawan, Didier Poinsot, Bruno Domenichini, Peter R. Schreiner, Andrey A. Fokin, Jean‐Cyrille Hierso. Nanodiamonds: Emergence of Functionalized Diamondoids and Their Unique Applications. 2014, 69-113. https://doi.org/10.1002/9781118870068.ch3
    29. Robert Richter, David Wolter, Tobias Zimmermann, Lasse Landt, Andre Knecht, Christoph Heidrich, Andrea Merli, Otto Dopfer, Philipp Reiß, Arno Ehresmann, Jens Petersen, Jeremy E. Dahl, Robert M. K. Carlson, Christoph Bostedt, Thomas Möller, Roland Mitric, Torbjörn Rander. Size and shape dependent photoluminescence and excited state decay rates of diamondoids. Phys. Chem. Chem. Phys. 2014, 16 (7) , 3070-3076. https://doi.org/10.1039/C3CP54570A
    30. Maria A. Gunawan, Jean-Cyrille Hierso, Didier Poinsot, Andrey A. Fokin, Natalie A. Fokina, Boryslav A. Tkachenko, Peter R. Schreiner. Diamondoids: functionalization and subsequent applications of perfectly defined molecular cage hydrocarbons. New J. Chem. 2014, 38 (1) , 28-41. https://doi.org/10.1039/C3NJ00535F
    31. Andrey A. Fokin, Ekaterina D. Butova, Anastasiya V. Barabash, Nhan N. Huu, Boryslav A. Tkachenko, Natalie A. Fokina, Peter R. Schreiner. Preparative Synthesis of Vinyl Diamondoids. Synthetic Communications 2013, 43 (13) , 1772-1777. https://doi.org/10.1080/00397911.2012.667491
    32. S. N. Yashkin. Molecular statistical calculation of thermodynamic characteristics of adsorption of polymantane molecules on the basis face of graphite. Russian Chemical Bulletin 2013, 62 (5) , 1131-1142. https://doi.org/10.1007/s11172-013-0156-4
    33. Márton Vörös, Tamás Demjén, Tibor Szilvási, Adam Gali. Tuning the Optical Gap of Nanometer-Size Diamond Cages by Sulfurization: A Time-Dependent Density Functional Study. Physical Review Letters 2012, 108 (26) https://doi.org/10.1103/PhysRevLett.108.267401
    34. P. A. Gunchenko, A. A. Fokin. Mechanisms of activation of C—H bonds in framework compounds: theory and experiment. Theoretical and Experimental Chemistry 2012, 47 (6) , 343-360. https://doi.org/10.1007/s11237-012-9226-1
    35. Andrey A. Fokin, Peter R. Schreiner. Selective Alkane CH Bond Substitutions: Strategies for the Preparation of Functionalized Diamondoids (Nanodiamonds). 2012, 317-350. https://doi.org/10.1016/B978-0-12-386540-3.00014-9
    36. Tatyana E. Shubina, Andrey A. Fokin. Hydrocarbon σ‐radical cations. WIREs Computational Molecular Science 2011, 1 (5) , 661-679. https://doi.org/10.1002/wcms.24
    37. Tsuyoshi Gushiken, Seiji Ujiie, Takashi Ubukata, Yasushi Yokoyama. Alkoxyphenyl-Substituted Symmetric Liquid Crystalline Diamantane Derivatives. Bulletin of the Chemical Society of Japan 2011, 84 (3) , 269-282. https://doi.org/10.1246/bcsj.20100259
    38. Jeremy E. P. Dahl, J. Michael Moldowan, Zhibin Wei, Paul A. Lipton, Peter Denisevich, Roy Gat, Shengao Liu, Peter R. Schreiner, Robert M. K. Carlson. Synthesis of Higher Diamondoids and Implications for Their Formation in Petroleum. Angewandte Chemie 2010, 122 (51) , 10077-10081. https://doi.org/10.1002/ange.201004276
    39. Jeremy E. P. Dahl, J. Michael Moldowan, Zhibin Wei, Paul A. Lipton, Peter Denisevich, Roy Gat, Shengao Liu, Peter R. Schreiner, Robert M. K. Carlson. Synthesis of Higher Diamondoids and Implications for Their Formation in Petroleum. Angewandte Chemie International Edition 2010, 49 (51) , 9881-9885. https://doi.org/10.1002/anie.201004276
    40. Lasse Landt, Matthias Staiger, David Wolter, Kathrin Klünder, Peter Zimmermann, Trevor M. Willey, Tony van Buuren, Daniel Brehmer, Peter R. Schreiner, Boryslav A. Tkachenko, Andrey A. Fokin, Thomas Möller, Christoph Bostedt. The influence of a single thiol group on the electronic and optical properties of the smallest diamondoid adamantane. The Journal of Chemical Physics 2010, 132 (2) https://doi.org/10.1063/1.3280388
    41. E. I. Bagrii, R. E. Safir, Yu. A. Arinicheva. Methods of the functionalization of hydrocarbons with a diamond-like structure. Petroleum Chemistry 2010, 50 (1) , 1-16. https://doi.org/10.1134/S0965544110010019
    42. Andrey A. Fokin, Pavel A. Gunchenko, Anatoliy A. Novikovsky, Tatyana E. Shubina, Boris V. Chernyaev, Jeremy E. P. Dahl, Robert M. K. Carlson, Alexander G. Yurchenko, Peter R. Schreiner. Photoacetylation of Diamondoids: Selectivities and Mechanism. European Journal of Organic Chemistry 2009, 2009 (30) , 5153-5161. https://doi.org/10.1002/ejoc.200900600
    43. Lasse Landt, Kathrin Klünder, Jeremy E. Dahl, Robert M. K. Carlson, Thomas Möller, Christoph Bostedt. Optical Response of Diamond Nanocrystals as a Function of Particle Size, Shape, and Symmetry. Physical Review Letters 2009, 103 (4) https://doi.org/10.1103/PhysRevLett.103.047402
    44. Hartmut Schwertfeger, Christian Würtele, Heike Hausmann, Jeremy E. P. Dahl, Robert M. K. Carlson, Andrey A. Fokin, Peter R. Schreiner. Selective Preparation of Diamondoid Fluorides [1]. Advanced Synthesis & Catalysis 2009, 351 (7-8) , 1041-1054. https://doi.org/10.1002/adsc.200800787
    45. Trevor M. Willey, Jonathan R.I. Lee, Jason D. Fabbri, Dongbo Wang, Michael H. Nielsen, Jason C. Randel, Peter R. Schreiner, Andrey A. Fokin, Boryslav A. Tkachenko, Natalie A. Fokina, Jeremy E.P. Dahl, Robert M.K. Carlson, Louis J. Terminello, Nicholas A. Melosh, Tony van Buuren. Determining orientational structure of diamondoid thiols attached to silver using near-edge X-ray absorption fine structure spectroscopy. Journal of Electron Spectroscopy and Related Phenomena 2009, 172 (1-3) , 69-77. https://doi.org/10.1016/j.elspec.2009.03.011
    46. Andrey A. Fokin, Peter R. Schreiner. Band gap tuning in nanodiamonds: first principle computational studies. Molecular Physics 2009, 107 (8-12) , 823-830. https://doi.org/10.1080/00268970802649625
    47. Andrey A. Fokin, Boryslav A. Tkachenko, Natalie A. Fokina, Heike Hausmann, Michael Serafin, Jeremy E. P. Dahl, Robert M. K. Carlson, Peter R. Schreiner. Reactivities of the Prism‐Shaped Diamondoids [1(2)3]Tetramantane and [12312]Hexamantane (Cyclohexamantane). Chemistry – A European Journal 2009, 15 (15) , 3851-3862. https://doi.org/10.1002/chem.200801867
    48. Dietmar Kuck. Molecules with Nonstandard Topological Properties: Centrohexaindane, Kuratowski's Cyclophane and Other Graph‐theoretically Nonplanar Molecules. 2009, 425-447. https://doi.org/10.1002/9783527627134.ch9
    49. Kathlyn A. Parker, Mark W. Ledeboer, Jeremy D. Pettigrew. Nitric Acid. 2009https://doi.org/10.1002/047084289X.rn022.pub2
    50. Ah-Young Jee, Minyung Lee. Surface functionalization and physicochemical characterization of diamond nanoparticles. Current Applied Physics 2009, 9 (2) , e144-e147. https://doi.org/10.1016/j.cap.2008.12.045
    51. Wenhua Zhang, Bin Gao, Jinlong Yang, Ziyu Wu, Vincenzo Carravetta, Yi Luo. Electronic structure of [121]tetramantane-6-thiol on gold and silver surfaces. The Journal of Chemical Physics 2009, 130 (5) https://doi.org/10.1063/1.3072334
    52. Hartmut Schwertfeger, Andrey A. Fokin, Peter R. Schreiner. “Diamonds are a chemist's best friend”: die großen Geschwister des Adamantans. Angewandte Chemie 2008, 120 (6) , 1038-1053. https://doi.org/10.1002/ange.200701684
    53. Hartmut Schwertfeger, Andrey A. Fokin, Peter R. Schreiner. Diamonds are a Chemist's Best Friend: Diamondoid Chemistry Beyond Adamantane. Angewandte Chemie International Edition 2008, 47 (6) , 1022-1036. https://doi.org/10.1002/anie.200701684
    54. Yayu Wang, Emmanouil Kioupakis, Xinghua Lu, Daniel Wegner, Ryan Yamachika, Jeremy E. Dahl, Robert M. K. Carlson, Steven G. Louie, Michael F. Crommie. Spatially resolved electronic and vibronic properties of single diamondoid molecules. Nature Materials 2008, 7 (1) , 38-42. https://doi.org/10.1038/nmat2066
    55. Natalie A. Fokina, Boryslav A. Tkachenko, Anika Merz, Michael Serafin, Jeremy E. P. Dahl, Robert M. K. Carlson, Andrey A. Fokin, Peter R. Schreiner. Hydroxy Derivatives of Diamantane, Triamantane, and [121]Tetramantane: Selective Preparation of Bis‐Apical Derivatives. European Journal of Organic Chemistry 2007, 2007 (28) , 4738-4745. https://doi.org/10.1002/ejoc.200700378
    56. K. Lenzke, L. Landt, M. Hoener, H. Thomas, J. E. Dahl, S. G. Liu, R. M. K. Carlson, T. Möller, C. Bostedt. Experimental determination of the ionization potentials of the first five members of the nanodiamond series. The Journal of Chemical Physics 2007, 127 (8) https://doi.org/10.1063/1.2773725
    57. W. L. Yang, J. D. Fabbri, T. M. Willey, J. R. I. Lee, J. E. Dahl, R. M. K. Carlson, P. R. Schreiner, A. A. Fokin, B. A. Tkachenko, N. A. Fokina, W. Meevasana, N. Mannella, K. Tanaka, X. J. Zhou, T. van Buuren, M. A. Kelly, Z. Hussain, N. A. Melosh, Z.-X. Shen. Monochromatic Electron Photoemission from Diamondoid Monolayers. Science 2007, 316 (5830) , 1460-1462. https://doi.org/10.1126/science.1141811
    58. Andrey A. Fokin, Peter R. Schreiner, Natalie A. Fokina, Boryslav A. Tkachenko, Heike Hausmann, Michael Serafin, Jeremy E. P. Dahl, Shenggao Liu, Robert M. K. Carlson. Functionalized Nanodiamonds. Part 4. Reactivity of [1(2,3)4]Pentamantane (T d ‐Pentamantane): A Nanoscale Model of Diamond.. ChemInform 2007, 38 (3) https://doi.org/10.1002/chin.200703069
    Download PDF
    Go to The Journal of Organic Chemistry
    Get e-Alerts
    Get e-Alerts

    The Journal of Organic Chemistry

    Cite this: J. Org. Chem. 2006, 71, 22, 8532–8540
    Click to copy citationCitation copied!
    https://doi.org/10.1021/jo061561x
    Published September 26, 2006
    Copyright © 2006 American Chemical Society
    Request reuse permissions

    Article Views

    1279

    Altmetric

    -

    Citations

    58
    Learn about these metrics

    Article Views are the COUNTER-compliant sum of full text article downloads since November 2008 (both PDF and HTML) across all institutions and individuals. These metrics are regularly updated to reflect usage leading up to the last few days.

    Citations are the number of other articles citing this article, calculated by Crossref and updated daily. Find more information about Crossref citation counts.

    The Altmetric Attention Score is a quantitative measure of the attention that a research article has received online. Clicking on the donut icon will load a page at altmetric.com with additional details about the score and the social media presence for the given article. Find more information on the Altmetric Attention Score and how the score is calculated.