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Within each series the cell parameters are the same for the three <jats:italic>R<\/jats:italic>, <jats:italic>S<\/jats:italic>, and <jats:italic>rac<\/jats:italic> compounds, except for the space group, which is centrosymmetric triclinic <jats:italic>P<\/jats:italic><jats:styled-content>$\\bar 1$<jats:inline-graphic xmlns:xlink=\"http:\/\/www.w3.org\/1999\/xlink\" xlink:href=\"graphic\/tex2gif-ueqn-1.gif\" xlink:title=\"equation image\"\/><\/jats:styled-content> for the racemic forms and noncentrosymmetric <jats:italic>P<\/jats:italic>1 for the enantiopure salts. In the racemic salt [(<jats:italic>rac<\/jats:italic>)\u2010<jats:bold>1<\/jats:bold>]<jats:sub>2<\/jats:sub>PF<jats:sub>6<\/jats:sub> the two enantiomers crystallize disordered on the same crystallographic site with a site occupational factor of 0.6:0.4, whereas this type of disorder is not possible in the enantiopure salts. Both s\u2010<jats:italic>cis<\/jats:italic> and s\u2010<jats:italic>trans<\/jats:italic> conformations, when taking into account the mutual orientation of the TTF and oxazoline moieties, are present in this first series. In sharp contrast, in the series of salts [<jats:bold>1<\/jats:bold>]<jats:sub>2<\/jats:sub>[Au(CN)<jats:sub>2<\/jats:sub>], only the s\u2010<jats:italic>trans<\/jats:italic> conformation is observed with no structural disorder. Theoretical calculations at the DFT level of theory revealed a very small energy difference between the two stable planar s\u2010<jats:italic>cis<\/jats:italic> and s\u2010<jats:italic>trans<\/jats:italic> conformations, which are both energy minima in either neutral or oxidized states. Single\u2010crystal conductivity measurements showed metallic\u2010like behavior for all the salts down to 220\u2013250\u2005K with a smooth increase in resistivity at lower temperatures. The conductivity at room temperature is 5\u2005S\u2009cm<jats:sup>\u22121<\/jats:sup> for [(<jats:italic>rac<\/jats:italic>)\u2010<jats:bold>1<\/jats:bold>]<jats:sub>2<\/jats:sub>PF<jats:sub>6<\/jats:sub>, in which disorder was observed, whereas for [(<jats:italic>R<\/jats:italic>)\u2010<jats:bold>1<\/jats:bold>]<jats:sub>2<\/jats:sub>PF<jats:sub>6<\/jats:sub> and [(<jats:italic>S<\/jats:italic>)\u2010<jats:bold>1<\/jats:bold>]<jats:sub>2<\/jats:sub>PF<jats:sub>6<\/jats:sub> the average value is around 100\u2005S\u2009cm<jats:sup>\u22121<\/jats:sup>. In the second series of salts the conductivity at room temperature is 125\u2013130\u2005S\u2009cm<jats:sup>\u22121<\/jats:sup> for [(<jats:italic>rac<\/jats:italic>)\u2010<jats:bold>1<\/jats:bold>]<jats:sub>2<\/jats:sub>[Au(CN)<jats:sub>2<\/jats:sub>] and [(<jats:italic>R<\/jats:italic>)\u2010<jats:bold>1<\/jats:bold>]<jats:sub>2<\/jats:sub>[Au(CN)<jats:sub>2<\/jats:sub>]. Extended H\u00fcckel band structure calculations revealed identical features for the three salts of the [<jats:bold>1<\/jats:bold>]<jats:sub>2<\/jats:sub>[Au(CN)<jats:sub>2<\/jats:sub>] series and are consistent with the electronic structures of quasi\u2010one\u2010dimensional conductors.<\/jats:p>","DOI":"10.1002\/chem.200901980","type":"journal-article","created":{"date-parts":[[2009,11,10]],"date-time":"2009-11-10T09:59:28Z","timestamp":1257847168000},"page":"528-537","source":"Crossref","is-referenced-by-count":47,"title":["Order Versus Disorder in Chiral Tetrathiafulvalene\u2010Oxazoline Radical\u2010Cation Salts: Structural and Theoretical Investigations and Physical Properties"],"prefix":"10.1002","volume":"16","author":[{"given":"Augustin\u2005M.","family":"Madalan","sequence":"first","affiliation":[]},{"given":"C\u00e9line","family":"R\u00e9thor\u00e9","sequence":"additional","affiliation":[]},{"given":"Marc","family":"Fourmigu\u00e9","sequence":"additional","affiliation":[]},{"given":"Enric","family":"Canadell","sequence":"additional","affiliation":[]},{"given":"Elsa\u2005B.","family":"Lopes","sequence":"additional","affiliation":[]},{"given":"Manuel","family":"Almeida","sequence":"additional","affiliation":[]},{"given":"Pascale","family":"Auban\u2010Senzier","sequence":"additional","affiliation":[]},{"given":"Narcis","family":"Avarvari","sequence":"additional","affiliation":[]}],"member":"311","published-online":{"date-parts":[[2009,12,28]]},"reference":[{"key":"e_1_2_6_1_2","unstructured":"\u00a0"},{"key":"e_1_2_6_2_2","doi-asserted-by":"publisher","DOI":"10.1021\/cr030641n"},{"key":"e_1_2_6_3_2","doi-asserted-by":"publisher","DOI":"10.1039\/B415940N"},{"key":"e_1_2_6_4_2","doi-asserted-by":"publisher","DOI":"10.1039\/b820598a"},{"key":"e_1_2_6_5_2","doi-asserted-by":"publisher","DOI":"10.1103\/PhysRevLett.87.236602"},{"key":"e_1_2_6_6_2","unstructured":"\u00a0"},{"key":"e_1_2_6_7_2","doi-asserted-by":"publisher","DOI":"10.1063\/1.1523895"},{"key":"e_1_2_6_8_2","doi-asserted-by":"publisher","DOI":"10.1016\/S0009-2614(02)01243-5"},{"key":"e_1_2_6_9_2","unstructured":"\u00a0"},{"key":"e_1_2_6_10_2","doi-asserted-by":"publisher","DOI":"10.1021\/ma030087j"},{"key":"e_1_2_6_11_2","doi-asserted-by":"publisher","DOI":"10.1021\/cm702875p"},{"key":"e_1_2_6_12_2","doi-asserted-by":"publisher","DOI":"10.1002\/adma.200500348"},{"key":"e_1_2_6_13_2","doi-asserted-by":"publisher","DOI":"10.1002\/ange.200704747"},{"key":"e_1_2_6_13_3","doi-asserted-by":"publisher","DOI":"10.1002\/anie.200704747"},{"key":"e_1_2_6_14_2","unstructured":"\u00a0"},{"volume-title":"Organic Superconductors (Including Fullerenes), Synthesis Structure, Properties and Theory","year":"1992","author":"Williams J. 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