Other Organic Ligands

510 Pages·1977·14.794 MB·English

by  Arthur E. Martell, Robert M. Smith (auth.)

Critical Stability Constants 3
Arthur Martell · Robert M. Smith
Other Organic Ligands
CRITICAL
STABILITY
CONSTANTS
Volume 3: Other Organic Ligands
CRITICAL STABILITY CONSTANTS
Volume 1 • Amino Acids
Volume 2 • Amines
Volume 3 • Other Organic Ligands
Volume 4 • Inorganic Complexes
CRITICAL
STABILITY
CONSTANTS
Volume 3: Other Organic Ligands
by Arthur E. Martell
and Robert M. Smith
Department of Chemistry
College of Science
Texas A & M University
College Station, Texas
SPRINGER SCIENCE+BUSINESS MEDIA, LLC
Library of Congress Cataloging in Publication Data
Martell, Arthur Earl, 1916-
Critical stabil ity constants.
On vol. 2 and 4 Smith's name appears first on t.p.
I ncludes bibliographical reterences.
CONTENTS: v. 1. Amino acids.-v. 2. Amines.-v. 3. Other organic
ligands-v. 4. lnorganic complexes.
1. Chemical equilibrium-Tables, etc. 2. Camplex compounds-Tables,
etc. I. Smith, Robert Martin, 1927- joint author. II. Title. [DNLM:
1. Amino acids. 2. Chemistry, Physical. QD503 M376c]
QD503.M37 541'.392 74-10610
ISBN 978-1-4757-1570-5 ISBN 978-1-4757-1568-2 (eBook)
DOI 10.1007/978-1-4757-1568-2
© 1977 Springer Science+Business Media New York
Originally published by Plenum Press, New York in 1977
All rights reserved
No part of this book may be reproduced, stored in a retrieval system, or transmitted,
in any form or by any means, electronic, mechanical, photocopying, microfilming,
recording, or otherwise, without written permission from the Publisher.
PREFACE
Over the past fifteen years the Commission on Equilibrium Data of the Analytical Division of the Inter
national Union of Pure and Applied Chemistry has been sponsoring a noncritical compilation of metal
complex formation constants and related equilibrium constants. This work was extensive in scope and
resulted in the publication of two large volumes of Stability Constants by the Chemical Society
(London). The first volume, edited by L. G. Sillen (for inorganic ligands) and by A. E. Martell (for
organic ligands), was published in 1964 and covered the literature through 1962. The second volume,
subtitled Supplement No. 1, edited by L. G. Sillen and E. Hogfeldt (for inorganic ligands) and by A. E.
Martell and R. M. Smith (for organic ligands), was published in 1971 and covered the literature up to
1969. These two large compilations attempted to cover all papers in the field related to metal complex
equilibria (heats, entropies, and free energies). Since it was the policy of the Commission during that
period to avoid decisions concerning the quality and reliability of the published work, the compilation
would frequently contain from ten to twenty values for a single equilibrium constant. In many cases
the values would differ by one or even two orders of magnitude, thus frustrating readers who wanted
to use the data without doing the extensive literature study necessary to determine the correct value of
the constant in question.
Because of difficulties of this nature, and because of the general lack of usefulness of a noncritical
compilation for teaching purposes and for scientists who are not sufficiently expert in the field of equ i
librium to carry out their own evaluation, we have decided to concentrate our efforts in this area
toward the development of a critical and unique compilation of metal complex equilibrium constants .
.1 \lthough it would seem that decisions between available sets of data must sometimes be arbitrary and
therefore possibly unfair, we have found the application of reasonable guidelines leads directly to the
elimination of a considerable fraction of the published data of doubtful value. Additional criteria and
procedures that were worked out to handle the remaining literature are described in the Introduction
of this book. Many of these methods are quite similar to those used in other compilations of critical
data.
In cases where a considerable amount of material has accumulated, it is felt that most of our critical
constants will stand the test of time. Many of the data listed, however, are based on only one or a very
few literature references and are subject to change when better data come along. It should be fully
understood that this compilation is a continually changing and growing body of data, and will be
revised from time to time as new results of these systems appear in the literature.
The scope of these tables includes the heats, entropies, and free energies of all reactions involving
Oiganic and inorganic ligands. The magnitude of the work is such that far more than a thousand book
pages will be required. In order that the material be available in convenient form, the amino acid
v
vi PREFACE
complexes are presented in Volume 1 and amine complexes (which do not contain carboxylic acid
functions) are included in Volume 2. The remaining organic complexes are the subject of Volume 3.
Volume 4 comprises the inorganic complexes.
Texas A&M University Arthur E. Martell
College Station, Texas Robert M. Smith
CONTENTS
I. Introduction. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . xi
II. Carboxylic acids
A. Mono-carboxylic acids. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 1
1. No other coordinating groups
2. With additional coordinating groups
a. Dihydrogen phosphate . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 23
b. Hydroxy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 24
c. Oxo....................................................... 65
d. Ester.... . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 67
e. Amido..................................................... 68
f. Alkyloxy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 69
g. Mercapto. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 73
h. Alkylthio. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 77
i. Alkylseleno. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 84
j. Ureido. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 88
k. Thiocarbamoyl . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 91
B. Di-carboxylic acids . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 92
1. No other coordinating groups
2. With additional coordinating groups
a. Hydroxy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 124
b. Oxo ....................................................... 131
c. Amido ..................................................... 132
d. Alkyloxy ................................................... 133
e. Mercapto. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 140
f. Alkylthio. .................................................. 142
g. Alkylseleno ................................................. 151
h. Alkyltelluro. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 154
i. Arsino. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 154
C. Tri-carboxylic acids ................................................. 158
D. Tetra-carboxylic acids ............................................... 167
Ill. Phosphorus acids
A. Hydrogen phosphates ............................................... 172
B. Phosphonic acids ................................................... 175
vii
viii CONTENTS
IV. Arsonic acids .......................................................... 180
V. Phenols
A. Mono-hydroxyphenols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 181
1. No other coordinating groups
2. With additional coordinating groups
a. Sulfa ...................................................... 184
b. Phosphono . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 184
c. Arsono . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 185
d. Carboxy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 186
e. Oxo ....................................................... 194
f. Ester . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 198
g. Amido ..................................................... 199
B. Di-hydroxyphenols ................................................. 200
1. No other coordinating groups
2. With additional coordinating groups
a. Sulfa ...................................................... 204
b. Arsono . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 208
c. Carboxy . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 208
d. Oxo ....................................................... 211
e. Alkyloxy ................................................... 211
C. Tri-hydroxyphenols. ................................................ 212
D. Fuchsones ........................................................ 214
E. Naphthols
1. Mono-hydroxynaphthols ......................................... 217
a. Nitrosonaphthols. ............................................ 217
b. Sulfonaphthols .......................................... : ... 229
c. Carboxy naphthols. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 232
2. Di-hydroxynaphthols ............................................ 233
a. Sulfonaphthols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 234
F. Hydroxyanthraquinones ............................................. 242
VI. Carbonyl ligands
A. Mono-oxo ligands . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 243
B. Di-oxo ligands ..................................................... 243
C. Hydroxycarbonyl ligands
1. Tropolones . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 250
2. Hydroxypyrones. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 255
3. Dihydroxybenzoquinones ......................................... 261
4. Squaric acid. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . .. . . . . . . . . . . . . . . . . . . . 263
5. Croconic acid .................................................. 264
6. Ascorbic acid ................................................... 264
VII. Alcohols
A. Glycols .......................................................... 266
B. Polyhydroxyligands. ................................................ 268
CONTENTS ix
C. Pentoses . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 271
D. Hexoses .......................................................... 274
VIII. Polyethers ............................................................ 278
I X. Thiols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 280
X. Thiocarboxylic acids .................................................... 284
XI. Unsaturated hydrocarbons
A. Ethenes .......................................................... 285
B. Ethynes .......................................................... 292
C. Nitrites .......................................................... 293
D. Benzenes. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 294
XII. Halides .............................................................. 300
XIII. Hydroxamic acids ...................................................... 301
XIV. Oximes .............................................................. 306
XV. Amides .............................................................. 310
XVI. Amidines ............................................................. 324
XV II. Protonation values for other I igands
A. Carboxylic acids ................................................... 329
B. Phosphorus acids ................................................... 344
C. Arsonic acids ...................................................... 346
D. Phenols .......................................................... 347
E. Carbonyl I igands . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 352
F. Alcohols . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 354
G. Thiols ........................................................... 355
H. Thiocarboxylic acids ................................................ 356
I. Sulfonic acids ..................................................... 356
J. Hydroxamic acids .................................................. 357
K. Ox imes . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 357
L. Nitro .compounds .................................................. 357
M. Amides .......................................................... 357
N. Biguanides ........................................................ 358
XV Ill. Ligands considered but not included
A. Carboxylic acids ................................................... 359