Molecular Rotation in the Solid Forms of Some Long-Chain Alcohols (original) (raw)

articleFebruary 1, 1949

Molecular Rotation in the Solid Forms of Some Long-Chain Alcohols

Click to copy article linkArticle link copied!

ACS Legacy Archive

Journal of the American Chemical Society

Cite this: J. Am. Chem. Soc. 1949, 71, 2

Click to copy citationCitation copied!

Published February 1, 1949

research-article

ACS Publications

Note: In lieu of an abstract, this is the article's first page.

Free first page

Cited By

Click to copy section linkSection link copied!

This article is cited by 83 publications.

  1. Antonela Ananiadou, Michalis Alagiannis, Martin Steinhart, Konstantinos Skobridis, George Floudas. Polymorphism of Crystalline Alcohols Under Nanoscale Confinement. The Journal of Physical Chemistry C 2022, 126 (38) , 16409-16420. https://doi.org/10.1021/acs.jpcc.2c04631
  2. Antonela Ananiadou, George Papamokos, Martin Steinhart, George Floudas. Nanometer Confinement Induces Nematic Order in 1-Dodecanol. The Journal of Physical Chemistry B 2020, 124 (47) , 10850-10857. https://doi.org/10.1021/acs.jpcb.0c08403
  3. U. Zammit, M. Marinelli, F. Mercuri and S. Paoloni. Analysis of the Order Character of the RII−RI and the RI−RV Rotator Phase Transitions in Alkanes by Photopyroelectric Calorimetry. The Journal of Physical Chemistry B 2010, 114 (24) , 8134-8139. https://doi.org/10.1021/jp102609y
  4. Urszula Domańska and, Marta Karolina Kozłowska, , Marek Rogalski, , Wojciech Skupiński. Solid + Liquid Equilibria of Isotactic Poly(1-butene) + n-Alkanes by Differential Scanning Calorimetry and Dynamic Methods. Industrial & Engineering Chemistry Research 2005, 44 (5) , 1592-1601. https://doi.org/10.1021/ie049556b
  5. Urszula Domańska and, Małgorzata Głoskowska. Experimental Solid + Liquid Equilibria and Excess Molar Volume of Alkanol + Octylamine Mixtures. Analysis in Terms of ERAS, DISQUAC, and Modified UNIFAC. Journal of Chemical & Engineering Data 2004, 49 (1) , 101-108. https://doi.org/10.1021/je0301895
  6. Urszula Domańska,, Ewa Bogel-Łukasik, and, Rafał Bogel-Łukasik. Solubility of 1-Dodecyl-3-methylimidazolium Chloride in Alcohols (C2−C12). The Journal of Physical Chemistry B 2003, 107 (8) , 1858-1863. https://doi.org/10.1021/jp021332o
  7. J. Cees van Miltenburg and, Harry A. J. Oonk, , Lourdes Ventola. Heat Capacities and Derived Thermodynamic Functions of 1-Octadecanol, 1-Nonadecanol, 1-Eicosanol, and 1-Docosanol between 10 K and 370 K. Journal of Chemical & Engineering Data 2001, 46 (1) , 90-97. https://doi.org/10.1021/je000048s
  8. Yan Dong, Tzu‐Li Liu, Shulin Chen, Prasad Nithianandam, Keyan Matar, Jinghua Li. A “Two‐Part” Resonance Circuit based Detachable Sweat Patch for Noninvasive Biochemical and Biophysical Sensing. Advanced Functional Materials 2023, 33 (6)https://doi.org/10.1002/adfm.202210136
  9. Miao Yao, Jun Nie, Yong He. Solid-state photopolymerization of long-chain vinyl carboxylates through binary molecular arrangement adjustment. Journal of Photochemistry and Photobiology A: Chemistry 2020, 401 , 112770. https://doi.org/10.1016/j.jphotochem.2020.112770
  10. Di Lu, Ying Yan, Raudel Avila, Irawati Kandela, Iwona Stepien, Min‐Ho Seo, Wubin Bai, Quansan Yang, Chenhang Li, Chad R. Haney, Emily A. Waters, Matthew R. MacEwan, Yonggang Huang, Wilson Z. Ray, John A. Rogers. Bioresorbable, Wireless, Passive Sensors as Temporary Implants for Monitoring Regional Body Temperature. Advanced Healthcare Materials 2020, 9 (16)https://doi.org/10.1002/adhm.202000942
  11. Prabir K. Mukherjee. Phase transitions among the rotator phases of the normal alkanes: A review. Physics Reports 2015, 588 , 1-54. https://doi.org/10.1016/j.physrep.2015.05.005
  12. H. Stuart, Th. Gast, E. Gast, W. Maier, A. W. Fink, E. Truscheit. Dielektrische Eigenschaften. 2013, 449-908. https://doi.org/10.1007/978-3-662-43287-7_1
  13. Hong Tang, Douglas C. MacLaren, Mary Anne White. New insights concerning the mechanism of reversible thermochromic mixtures. Canadian Journal of Chemistry 2010, 88 (11) , 1063-1070. https://doi.org/10.1139/V10-069
  14. Urszula Domańska, Małgorzata Marciniak. Experimental (solid+liquid) phase equilibria of (alkan-1-ol+benzonitrile), (amine+benzonitrile) binary mixtures, and (decan-1-ol+decylamine+benzonitrile) ternary mixtures. Fluid Phase Equilibria 2007, 251 (2) , 161-166. https://doi.org/10.1016/j.fluid.2006.11.012
  15. Urszula Domańska, Małgorzata Marciniak. Experimental (solid + liquid) or (liquid + liquid) phase equilibria of (amine + nitrile) binary mixtures. The Journal of Chemical Thermodynamics 2007, 39 (2) , 247-253. https://doi.org/10.1016/j.jct.2006.07.008
  16. U. Domańska, M. Marciniak. Experimental solid–liquid equilibria for systems containing alkan-1-ol+1,3-diaminopropane. Fluid Phase Equilibria 2005, 235 (1) , 30-41. https://doi.org/10.1016/j.fluid.2005.07.009
  17. Urszula Domańska, Ewa Bogel‐Łukasik, Rafał Bogel‐Łukasik. 1‐Octanol/Water Partition Coefficients of 1Alkyl‐3‐methylimidazolium Chloride. Chemistry – A European Journal 2003, 9 (13) , 3033-3041. https://doi.org/10.1002/chem.200204516
  18. Prabir K. Mukherjee. Elastic properties of the rotator phases of pentacosane C25H52. The Journal of Chemical Physics 2002, 116 (24) , 10787-10793. https://doi.org/10.1063/1.1479711
  19. U Domańska, J Łachwa. (Solid + liquid) phase equilibria of binary mixtures containing N-methyl-2-pyrrolidinone and long-chain n-alkanols at atmospheric pressure. Fluid Phase Equilibria 2002, 198 (1) , 1-14. https://doi.org/10.1016/S0378-3812(01)00752-X
  20. Shoji Fukushima, Michihiro Yamaguchi. Physical Chemistry of Cetyl Alcohol: Occurrence and Function of Liquid Crystals in O/W Creams. 2001, 1-98. https://doi.org/10.1007/978-1-4615-1223-3_1
  21. Prabir K. Mukherjee, Moshe Deutsch. Landau theory of the R II - R I - R V rotator phases of alkanes. Physical Review B 1999, 60 (5) , 3154-3162. https://doi.org/10.1103/PhysRevB.60.3154
  22. Paul Ruelle, Ulrich W Kesselring. Article. Canadian Journal of Chemistry 1998, 76 (5) , 553-565. https://doi.org/10.1139/v98-074
  23. U. Domańska, J.A. Gonzalez. Solid-liquid equilibria for systems containing long-chain 1-alkanols III. Experimental data for 1-tetradecanol, 1-hexadecanol, 1-octadecanol or 1-icosanol + 1-butanol, 1-hexanol, 1-octanol or 1-decanol mixtures. Characterization in terms of DISQUAC. Fluid Phase Equilibria 1997, 129 (1-2) , 139-163. https://doi.org/10.1016/S0378-3812(96)03150-0
  24. E. B. Sirota, X. Z. Wu. The rotator phases of neat and hydrated 1-alcohols. The Journal of Chemical Physics 1996, 105 (17) , 7763-7773. https://doi.org/10.1063/1.472559
  25. U. Domańska, J.A. González. Solid-liquid equilibria for systems containing long-chain 1-alkanols. II. Experimental data for 1-dodecanol, 1-tetradecanol, 1-hexadecanol, 1-octadecanol or 1-eicosanol + CCl4 or + cyclohexane mixtures. Characterization in terms of DISQUAC. Fluid Phase Equilibria 1996, 123 (1-2) , 167-187. https://doi.org/10.1016/S0378-3812(96)90023-0
  26. U. Domańska, J.A. González. Solid-liquid equilibria for systems containing long-chain 1-alkanols I. Experimental data for 1-dodecanol, 1-tetradecanol, 1-hexadecanol, 1-octadecanol or 1-icosanolbenzene or toluene mixtures. Characterization in terms of DISQUAC. Fluid Phase Equilibria 1996, 119 (1-2) , 131-151. https://doi.org/10.1016/0378-3812(95)02861-7
  27. Urszula Domańska. Measurement and correlation of the solubility of 1-alkanols (C14, C16), in n-alkanes (C7C16). Fluid Phase Equilibria 1996, 114 (1-2) , 175-188. https://doi.org/10.1016/0378-3812(95)02819-6
  28. J. Wang, W. H. Meyer, G. Wegner. Synthesis and solid‐state properties of comb‐like ionenes. Acta Polymerica 1995, 46 (3) , 233-240. https://doi.org/10.1002/actp.1995.010460304
  29. H. Kobayashi, N. Nakamura. Phase Transition of 1,16‐Hexadecanediol. Crystal Research and Technology 1995, 30 (4) , 495-500. https://doi.org/10.1002/crat.2170300413
  30. Urszula Domanska, Jolanta Rolińska. Measurement and correlation of the solubility of n-alkanols (C18, C20) in n-alkanes (C7–C16). Fluid Phase Equilibria 1993, 86 , 233-250. https://doi.org/10.1016/0378-3812(93)87179-5
  31. H. Kobayashi, N. Nakamura. New Temperature Control Apparatus for X‐ray Experiments. Crystal Research and Technology 1993, 28 (5) , 717-721. https://doi.org/10.1002/crat.2170280524
  32. Andrzej Ksia̧żczak. Vapour pressures of binary three-phase (solid + liquid + vapour) mixtures VII. Melting temperatures of the solid phases of n-dodecan-1-ol. The Journal of Chemical Thermodynamics 1991, 23 (11) , 1091-1096. https://doi.org/10.1016/S0021-9614(05)80115-6
  33. Ch. Wohlfahrt. 2 Pure Liquids: Data. 1991, 5-228. https://doi.org/10.1007/10047452_2
  34. Ch. Wohlfahrt. 2 Pure Liquids: References. 1991, 229-245. https://doi.org/10.1007/10047452_3
  35. Urszula Domańska. Solubility of n-alkanols (C16,C18,C20) in binary solvent mixtures. Fluid Phase Equilibria 1989, 46 (2-3) , 223-248. https://doi.org/10.1016/0378-3812(89)80037-8
  36. R. Lenc. Positron lifetimes in n-hexadecanol-1. Chemical Physics Letters 1985, 114 (2) , 229-232. https://doi.org/10.1016/0009-2614(85)85092-2
  37. F. Cangelosi, M. T. Shaw. A REVIEW OF HYDROGEN BONDING IN SOLID POLYMERS: STRUCTURAL RELATIONSHIPS, ANALYSIS, AND IMPORTANCE. Polymer-Plastics Technology and Engineering 1983, 21 (1) , 13-98. https://doi.org/10.1080/03602558308070020
  38. T. Goworek, C. Rybka, R. Wasiewicz, J. Wawryszczuk. Positron annihilation and phase transitions in n-octadecanol. Chemical Physics Letters 1982, 92 (2) , 202-204. https://doi.org/10.1016/0009-2614(82)80106-1
  39. N. Kirov, M. P. Fontana, F. Cavatorta, H. Ratajczak. IR, FIR, Ramna and Thermodynamic Investigations of p-n -Alkokybenzoic Acides in Their Solid, Mesomorphic and Isotropic Phases. Molecular Crystals and Liquid Crystals 1981, 75 (1) , 303-320. https://doi.org/10.1080/00268948108073622
  40. Kazutoshi Iwamoto, Yukio Ohnuki, Kiyoshi Sawada, Manabu Senō. Solid-Solid Phase Transitions of Long-Chain n -Alkyltrimethylammonium Halides. Molecular Crystals and Liquid Crystals 1981, 73 (1-2) , 95-103. https://doi.org/10.1080/00268948108076264
  41. D. Precht. Präparatschonende Elektronenbeugungsuntersuchungen an Tripalmitineinkristallen. Fette, Seifen, Anstrichmittel 1979, 81 (6) , 227-233. https://doi.org/10.1002/lipi.19790810602
  42. V. Mahadevan. Fatty alcohols: Chemistry and metabolism. Progress in the Chemistry of Fats and other Lipids 1977, 15 (4) , 255-299. https://doi.org/10.1016/0079-6832(77)90010-6
  43. G.M Eccleston. The structure and rheology of pharmaceutical and cosmetic creams. Cetrimide creams; The influence of alcohol chain length and homolog composition. Journal of Colloid and Interface Science 1976, 57 (1) , 66-74. https://doi.org/10.1016/0021-9797(76)90176-4
  44. C. Mosselman, J. Mourik, H. Dekker. Enthalpies of phase change and heat capacities of some long-chain alcohols. Adiabatic semi-microcalorimeter for studies of polymorphism. The Journal of Chemical Thermodynamics 1974, 6 (5) , 477-487. https://doi.org/10.1016/0021-9614(74)90009-3
  45. M. A. Al‐Mamun. Study of binary systems of long chain alcohols and acids. Journal of the American Oil Chemists' Society 1974, 51 (5) , 229-233. https://doi.org/10.1007/BF02632900
  46. L. Glasser, J. Crossley, C. P. Smyth. Microwave Absorption and Molecular Structure in Liquids. LXXIX. Dielectric Behavior and Association of Some Normal Alcohols in n -Heptane Solution. The Journal of Chemical Physics 1972, 57 (9) , 3977-3986. https://doi.org/10.1063/1.1678870
  47. M. I. Valic, M. M. Pintar. NMR of proton conductor borax. physica status solidi (b) 1970, 42 (2) , 661-667. https://doi.org/10.1002/pssb.19700420219
  48. B. Ellis, A. S. C. Lawrence, M. P. Mc.Donald, W. E. Peel. The Investigation of Lipid-Water Systems, Part 3. Nuclear Magnetic Resonance in the Mono-Octanoin-Deuterium Oxide System. 1970, 277-288. https://doi.org/10.1007/978-1-4684-8214-0_20
  49. V. A. Tolkachev, A. D. Milov, V. K. Ermolaev, A. S. Chernobrov. Interlayer polarization in crystalline glycerine containing small additions of water. Journal of Structural Chemistry 1970, 10 (5) , 685-689. https://doi.org/10.1007/BF00743949
  50. V. L. Khodzhaeva. Study of liquid crystalline state of p-n-alkyloxybenzoic acids according to their IR absorption spectra. Bulletin of the Academy of Sciences of the USSR Division of Chemical Science 1969, 18 (11) , 2257-2262. https://doi.org/10.1007/BF00906490
  51. M. E. Baird, G. T. Goldsworthy, C. J. Creasey. Low frequency dielectric behavior of polyamides. Journal of Polymer Science Part B: Polymer Letters 1968, 6 (10) , 737-742. https://doi.org/10.1002/pol.1968.110061011
  52. G. Klages, K. Kreuter. Dielektrisches Relaxationsspektrum von Polyamid mit adsorbiertem Wasser und Methanol. Kolloid-Zeitschrift und Zeitschrift für Polymere 1966, 208 (1) , 15-22. https://doi.org/10.1007/BF01499861
  53. Koichi Hirano. The Mechanism of the Electrical Conduction in Solid Acetamide. Bulletin of the Chemical Society of Japan 1965, 38 (5) , 842-845. https://doi.org/10.1246/bcsj.38.842
  54. Sachio Tsugane, Miyoshi Haradome, Ryuichi Hioki. Formation and Dielectric Properties of Glass in the System As-Te. Japanese Journal of Applied Physics 1965, 4 (2) , 77. https://doi.org/10.1143/JJAP.4.77
  55. M. Tasumi, T. Shimanouchi, A. Watanabe, R. Goto. Infrared spectra of normal higher alcohols—I. Spectrochimica Acta 1964, 20 (4) , 629-666. https://doi.org/10.1016/0371-1951(64)80060-6
  56. F. L. Breusch, E. Ulusoy. Physikalische Eigenschaften homologer kristallisierter Reihen mit alternierendem und nicht alternierendem Schmelzpunkt. Fette, Seifen, Anstrichmittel 1964, 66 (10) , 739-742. https://doi.org/10.1002/lipi.19640661001
  57. S. Maričić, V. Pravdić, Z. Veksli. Proton conductivity in borax, Na2[B4O5(OH)4]-8H2O. Journal of Physics and Chemistry of Solids 1962, 23 (11) , 1651-1659. https://doi.org/10.1016/0022-3697(62)90248-2
  58. Herbert Athenstaedt. Mesomorphe Ordnungszust�nde biologisch bedeutsamer Stoffe. Die Naturwissenschaften 1962, 49 (19) , 433-443. https://doi.org/10.1007/BF00632132
  59. Akira Watanabe. Synthesis and Physical Properties of Normal Higher Primary Alcohols. IV. Thermal and X-Ray Studies on the Polymorphism of the Alcohols of Even Carbon Numbers from Dodecanol to Tetratriacontanol. Bulletin of the Chemical Society of Japan 1961, 34 (11) , 1728-1734. https://doi.org/10.1246/bcsj.34.1728
  60. J. Naveau. Recherches Expérimentales sur le Polymorphisme des Corps Organiques. Bulletin des Sociétés Chimiques Belges 1961, 70 (11-12) , 662-689. https://doi.org/10.1002/bscb.19610701105
  61. Kenjiro Asai. On the Anomalous Dispersion of n-Primary Alcohols. Journal of the Physical Society of Japan 1959, 14 (8) , 1084-1090. https://doi.org/10.1143/JPSJ.14.1084
  62. Mikio Takeyama. On the Dielectric Properties of α-phase n-Higher Alcohols and Associated Electromotive Force. Journal of the Physical Society of Japan 1957, 12 (10) , 1167-1168. https://doi.org/10.1143/JPSJ.12.1167
  63. Mitsuo Ida. On the Dielectric Anomaly of n -Higher Alcohols in the “Waxy State”. Journal of the Physical Society of Japan 1956, 11 (10) , 1121-1121. https://doi.org/10.1143/JPSJ.11.1121
  64. Hachiro Komatsu. Proton Magnetic Resonance Absorption Spectra of Long Chain Normal Primary Alcohol of Probable Carbon Number 32. Journal of the Physical Society of Japan 1956, 11 (7) , 755-759. https://doi.org/10.1143/JPSJ.11.755
  65. D. Chapman. Infra-red spectroscopy applied to studies of polymorphism. Spectrochimica Acta 1956, 11 , 609-617. https://doi.org/10.1016/S0371-1951(56)80103-3
  66. Toshiaki Takamatsu. A New Dielectric Dispersion in Long-Chain Normal Primary Alcohol of Probable Carbon Number 32 at Lower Temperature Phase. Journal of the Physical Society of Japan 1955, 10 (12) , 1049-1054. https://doi.org/10.1143/JPSJ.10.1049
  67. Susumu Kurokawa. Modifications of Normal Fatty Acid Amides. Bulletin of the Chemical Society of Japan 1955, 28 (9) , 660-664. https://doi.org/10.1246/bcsj.28.660
  68. Kenjiro Asai, Eiji Yoda, Sueo Yamanaka. On the Anomaly of the Dielectric Properties of n -Higher Alcohols. Journal of the Physical Society of Japan 1955, 10 (8) , 634-642. https://doi.org/10.1143/JPSJ.10.634
  69. Kenjiro Asai. On Chemical Change of n-Higher Alcohol Caused by the Influence of Strong Electric Field. Journal of the Physical Society of Japan 1955, 10 (8) , 716-718. https://doi.org/10.1143/JPSJ.10.716
  70. . Studies on the Cuticle of the Grasshopper Melanoplus bivittatus (Say) (Orthoptera: Acrididae): III. On the Physical Nature of the Transition Region of Insect Waxes. The Canadian Entomologist 1955, 163-171. https://doi.org/10.4039/Ent87163-4
  71. R. Philippe, A. M. Piette. Recherches de Stoechiométrie VII( 1 ) Contribution à l'étude de la constante diélectrique des composés organiques purs. Bulletin des Sociétés Chimiques Belges 1955, 64 (9-10) , 600-627. https://doi.org/10.1002/bscb.19550640910
  72. C. W. BUNN, E. R. HOWELLS. Structures of Molecules and Crystals of Fluoro-Carbons. Nature 1954, 174 (4429) , 549-551. https://doi.org/10.1038/174549a0
  73. Sukeaki Hosoya. On the Transition Temperature of Molecular Rotation in Long-Chain Compounds With the Discontinuous Model. Journal of the Physical Society of Japan 1954, 9 (4) , 524-530. https://doi.org/10.1143/JPSJ.9.524
  74. Ryoiti Kiriyama, Shigeru Yabumoto, Isamu Nitta. Dielectric Behaviour of Crystalline Pentaerythritol. Bulletin of the Chemical Society of Japan 1954, 27 (2) , 115-119. https://doi.org/10.1246/bcsj.27.115
  75. C. Brot, M. Magat, Mme L. Reinisch. Sur la dispersion diélectrique dans le domaine décimétrique et centimétrique. Kolloid-Zeitschrift 1953, 134 (2-3) , 101-134. https://doi.org/10.1007/BF01521619
  76. Shoji Kojima, Shizuko Ogawa. Proton Magnetic Resonance Absorption in Cetyl Alcohol. Journal of the Physical Society of Japan 1953, 8 (3) , 283-287. https://doi.org/10.1143/JPSJ.8.283
  77. John D. Hoffman. Hindered Intermolecular Rotation in the Solid State: Thermal and Dielectric Phenomena in Long-Chain Compounds. The Journal of Chemical Physics 1952, 20 (4) , 541-549. https://doi.org/10.1063/1.1700488
  78. Robert W. Crowe, John D. Hoffman, Charles P. Smyth. A New Type of Disorder Affecting the Dielectric Properties of Long-Chain Esters. The Journal of Chemical Physics 1952, 20 (4) , 550-555. https://doi.org/10.1063/1.1700489
  79. Yoshinobu Kakiuchi. A Statistical Theory of Molecular Rotation in Normal Solid Hydrocarbons and Alcohols. Journal of the Physical Society of Japan 1951, 6 (5) , 313-320. https://doi.org/10.1143/JPSJ.6.313
  80. Yoshinobu Kakiuchi, Hachiro Komatsu, Susumu Kyoya. Proton Conduction through Solid Alcohols due to Molecular Rotation. Journal of the Physical Society of Japan 1951, 6 (5) , 321-328. https://doi.org/10.1143/JPSJ.6.321
  81. Tosio Sakurai. On the Transformation of Long Chain Acid Amides. Journal of the Physical Society of Japan 1951, 6 (3) , 199-200. https://doi.org/10.1143/JPSJ.6.199
  82. Yoshinobu Kakiuchi, Tosio Sakurai, Tadasu Suzuki. Anomalous Specific Heat and Molecular Rotation in Normal Solid Alcohols. Journal of the Physical Society of Japan 1950, 5 (5) , 369-375. https://doi.org/10.1143/JPSJ.5.369
  83. Yoshinobu Kakiuchi, Tosio Sakurai. Anomalous Specific Heat and Molecular Rotation in Solid Normal Hexadecyl Alcohol. Journal of the Physical Society of Japan 1949, 4 (4-6) , 365-365. https://doi.org/10.1143/JPSJ.4.365

Journal of the American Chemical Society

Cite this: J. Am. Chem. Soc. 1949, 71, 2

Click to copy citationCitation copied!

Published February 1, 1949

Altmetric

-

Citations

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.