Contribution of the intramolecular hydrogen bond to the shift of the pKa value and the oxidation potential of phenols and phenolate anions.
Kanamori, Daisuke; Furukawa, Atsushi; Okamura, Taka-aki; Yamamoto, Hitoshi; Ueyama, Norikazu; Organic & biomolecular chemistry 3 (2005) 1453–1459; doi:10.1039/b419361j

data_7150133
_publ_section_title
;
 Contribution of the intramolecular hydrogen bond to the shift of the
 pKa value and the oxidation potential of phenols and phenolate anions.
;
_journal_issue                   8
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1453
_journal_page_last               1459
_journal_paper_doi               10.1039/b419361j
_journal_volume                  3
_journal_year                    2005
_chemical_formula_moiety         'C11 H14 N O2, C8 H20 N, H2 O'
_chemical_formula_sum            'C19 H36 N2 O3'
_chemical_formula_weight         340.50
_chemical_name_systematic
;
?
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                97.147(15)
_cell_angle_beta                 92.285(15)
_cell_angle_gamma                109.753(14)
_cell_formula_units_Z            2
_cell_length_a                   10.0678(16)
_cell_length_b                   12.211(3)
_cell_length_c                   9.0829(12)
_cell_measurement_reflns_used    9
_cell_measurement_temperature    298
_cell_measurement_theta_max      13.7
_cell_measurement_theta_min      13.1
_cell_volume                     1038.7(4)
_computing_cell_refinement       WinAFC
_computing_data_collection       WinAFC
_computing_data_reduction        'teXsan Ver. 1.11'
_computing_publication_material  'teXsan Ver. 1.11'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    MULTAN88
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku AFC7R'
_diffrn_measurement_method       \w-2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0346
_diffrn_reflns_av_sigmaI/netI    0.2334
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5729
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.68
_diffrn_standards_decay_%        0.53
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.089
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.047
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4752
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.3179
_refine_ls_R_factor_gt           0.0688
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0800P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1691
_refine_ls_wR_factor_ref         0.2319
_reflns_number_gt                1179
_reflns_number_total             4752
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b419361j-ccdc.txt
_cod_data_source_block           1'ONEt4
_cod_original_cell_volume        1038.8(3)
_cod_original_sg_symbol_Hall     '-P 1         '
_cod_original_sg_symbol_H-M      'P -1         '
_cod_database_code               7150133