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Book Review Die Antibiotica (The antibiotics). Edited by R. Brunner and G. Machek. Vol. II. Die Mittleren Antibiotica (The medial antibiotics)

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Use of an excess of the phosphine and simultaneous reduction with sodium amalgan gives the reddish-brown, halogenfree, binuclear compound Co2(N0)2[C2H4(P(C6H5)2)213.
The IR spectra of all the compounds are discussed. Z . an[Rd 533 IE]
org. allg. Chem. 342, 93 (1966) / -Sch.
albumin and affords an antigen for determination of chloramphenicol antibodies. 10-5 g (= 4x10-4 mole) of chloramphenicol suffices for detection by quantitative complement
fixation. , Science (Washington) 152, 203 (1966) / -De.
[Rd 538 IE]
Phosphorus-aluminum compounds with pentaeoordinated aluminum have been described by D. F. Clemens, H . H. Sisler,
and W. S . Brey j r . Triethylaluminum with, for instance,
tetraphenyldiphosphine or bis(dipheny1phosphino)methylamine gives the complexes ( I ) (m.p. 99-101 “C, yield 60 %)
and ( 2 ) (m.p. 130-132”C, yield 80 %), respectively. The
authors conclude from I R and N M R measurements that the
products contain pentacoordinated aluminum.
New thermostable aromatic polyquinazolinediones have been
synthesized by N . Yodu, R . Nukanishi, and M . Krrrihortr.
Condensation of aromatic diisocyanates (e.g. p-phenylene
diisocyanate) with 4,4’-diamino-3,3’-biphenyldicarboxylic
acid in the melt or in solution at temperatures of up to 180 “C
yields a polyurea ( I ) , which, when heated in vacuum at 230
to 320°C, undergoes cyclodehydration to a polymer (2)
containing 2-imino-6H- 2,3 - dihydro[l,3]benzoxazine-6-one
groups. Further heating leads to intramolecular iearrangement to the thermodynamically more stable polyquinazolinedione ( 3 ) . When heated in air up to 650°C at 6 ° C min the
polymer ( 3 ) , the structure of which has been confirmed by I R
On interaction of bis(dipheny1phosphino)amine and triethylaluminum, ethane is evolved and a dimeric compound is
formed for which structure ( 3 ) with pentacoordinated
aluminum is proposed. Reaction of tetramethyldiphosphine
with triethylaluminum, however, affords a 1 :2 adduct
(CH3)zP- P(CH&.2AI(CzH5)3
(b.p. 102°C/0.1 mm)
containing the usual tetracoordinated aluminum. This
difference is ascribed to the higher basicity of tetramethyldiphosphine than of tetraphenyldiphosphine. ,’ Inorg. Chem.
5 , 527 (1966) -Sch.
[Rd 537 IE]
Chloramphenicol-specific antibodies have been observed by
R . N. Hamburger in immunized rabbits. The formation of
the antibody was demonstrated by precipitin- and complement-fixation reactions with “reduced chloramphenicol”,
namely, D-threo-1-p-aminophenyl-2-dichloroacetamido-l,3f 3)
propanediol ( I ) that has been coupled to rabbit-serum
albumin. Immunization of the rabbits was effected with ( I )
analysis, exhibits a weight loss of only 20 x. Under nitrogen
that had been coupled by diazotization to ox y-globulin.
this weight loss occurs only at 860 “C. These polymeis are also
Reduced chloramphenicol couples also with human serum
highly resistant to heat. The polyquinazolinediones are stable
to strong acids and alkalis, and insoluble in most organic
solvents, but soluble in fuming nitric acid and cold concentrated sulfuric acid. / J. Polymer Sci. B, Polymer Letters 4 ,
7 1 (1966) 1 -HI.
[Rd 555 IEi
Die Antibiotica (The antibiotics). Edited by R. Brunner and
G . Muchek. Vol. 11. Die Mittleren Antibiotica (The medial
antibiotics). Verlag Hans Carl, Nuremberg 1965. 1st ed.,
xvi, 992 pp., bound D M 145.- (cu. $36).
This ambitious book on antibiotics, which was written by a
group of Austrian scientists, deals with the chemistry, biochemistry, and clinical use of these compounds, and is the
first comprehensive German-language work on this important class of substances. The present second volume of
the three-volume handbook contains detalled chapters on
macrolides, amino acids and oligopeptides, polypeptides,
peptolids, antibiotics containing sugars, and polyenes. Special
antibiotics containing nitrogen heterocycles and antibiotics
with special structures are also discussed. Other chapters deal
with the use of antibiotics in animal nutrition, in the conservation of foods, and in the protection of plants. Recent
studies on resistance and on semi-synthetic penicillins are
discussed in an appendix.
In the individual chapters, experts describe the chemistry,
fermentation and biosynthesis, methods of determination.
resorption, distribution and elimination, action spectra,
action mechanisms, and toxicities of the compounds: their
use in human and veferinary medicine is described in particular detail.
More emphasis on stereorhemistry would have been desirable
in many places, e.p in the discussion of the macrolides. A
hydroxyl group has been omitted from the open-chain
formula of nleandrose on page 56. While the text is otherwise
very lucid, the description of attempts to elucidate the configuration of cycloheximtde (p. 630) is rather confusing. The
formula given OP this page is that of cis-(-)-2,4-dimethylcyclohexanone. Contrary to the statement on page 891. the
repressor is nowadays regarded as an allosteric protein or as
a compound of such a protein with RNA.
The book is outstanding in its layout and contents, and
should prove a mine of information for anyone concerned
Angew. Chem. internut. Edit.
Vol. 5 (1966)
with any problem in the antibiotics field, particularly since
publications that are difficult to obtain are also considered.
The literature is covered in part up to 1964, including many
patent references. The printing and presentation of the book
are very good. However, it would have been better to reproduce the formulae from drawings rather than by typesetting. The volume contains a detailed author and subject
H . Grisebncli
[NB 520 IE]
whereas even first-year chemistry students are taught that
electrons cannot disappear in redox reactions. Oxidation
numbers and (formal) ionic charges also are mixed u p
indiscriminately, as in the examples:
.4dvances in Inorganic Chemistry and Radiochemistry. Vol. 7.
Edited by H . Emelr‘us and A . Slinrpe. Academic Press,
New York-London 1965. 1st ed., 449 pp.. several illustrations, S15.50.
The present volume[*1 reflects a general unrest in current
inorganic chemical research, which is overlapping to an
increasing extent with the marginal fields of organic chemistry. Thus only two of the six contributions are devoted to
pure inorganic chemistry, the “Halides of Phosphorus,
Arsenic, Antimony, and Bismuth” by L . Kolditz, and the
“Hydride Complexes of the Transition Metals” by M . L. H .
Green and D. J . Jones. The organic component makes an
appearance in “Phthalocyanines” by A . B. P. Lever (despite
the fact that this contribution deals with metal-nitrogen
bonds), becomes more prominent in “Organoaluminum
Compounds” by R . Koster and P . Birrger and in “Carbosilanes” by G. Fritz, J . Grobe, and D. Kummer, and finally
becomes dominant in the “Reactions of Che!ated Organic
Ligands” by Q u . Fernondo.
The presentation and layout of this volume, as af the earlier
ones, is impeccable. Special mention should be made of the
editors’ constant efforts to include contributions by seecialists
from all over the world.
The first five contributions named above are consistent with
th-, high regard in which the “Advances ’ are held. However,
the article on “Reactioas of Chelated Organic Ligands”
leaves one with the impression of having been carried back a
century. The ignorance and indifference shown in this
article regarding the complicated and versatile bonding,
valence, and nomenclature rules for the 103 “inorganic”
elements could scarcely be surpassed.
Thus every bond, whether ionic or covalent, coordinate,
dative back-donation, or hydrogen bond, is indicated by a
valence line. Lone electron pairs are not shown, so that the
reader is left to deduce the origin of the bonding electrons
for himself. This is possible with some loss of time except
where the author, from a desire to surround each carbon
atom with four valence lines and each nitrogen atom with
three, presents completely new structural formulae, as on
p. 206 for bis(diacetyldioximato)nickel(u) (“Ni dimethyl-
glyoxime”). Here the diacetyldioxime has become an ethylene
derivative, and if one lone electron pair is assigned to each
N atom to avoid an electron sextet, the Ni atom must supply
at least four electrons for the bonds to the N atoms.According
to the author, this complex forms a chlorine adduct with
hydrogen chloride :
(C4H702Nz)~Ni 2 HCI
+ (C~HSO~N~)~N~.CI~
Similarly, the reaction of manganese(u1) ion with oxalate ion
is reported (p. 240) to proceed, via a chelate, by regrouping
of bonds, and via free-radical states, according to the overall
equation :
2 C02
- Mn2’
[*I Vol. 5 is reviewed in Angew. Chem. 77, 63 (1965); Angew.
Chem. internat. Edit. 4, 102 (1965), Vcll. 6 in Angew. Chem. 78,
500 (1966); Angew. Chem. internat. Edit. 5, 530 (1966).
Angew. Chem. internat. Edit. / Vol. 5 (1966)
No. 10
Of the five equations in the scheme ( L X X X I I I ) on p. 243.
four do not balance; careful perusal of the article rcvcal5 an
abundance of other errors and absurdities.
T o protect the reputation of the “Advances”, the cciitor5
should in future have thecourage to reject such contributions.
or at least take the patience to edit them carefully.
[NB 504 I El
U . Wannngtrt
The Ring Index
A List of Ring Systems Used in Organic
Chemistry. Supplement I11 (1962-1963) to the 2nd
edition. Rings 11 525-14265. American Chemical Society.
Washington 1965. 1st ed., vi, 546 pp., numerous illustrations, S10.00.
The third supplement to the second edition of the Ring Index
has now been publishedr*l. It contains all the new ring
systems described in the literature and referred to in Chemical
Abstracts between January 1, 1962 and December 31, 1963.
This amounts to a total of 2741 compounds, whereas the
corresponding figures for 1960!1961 and 1957-1959 were
about 1800 and 2000, respectively. This again reflects the
accelerated growth of knowledge in the natural scienc,eS The
ring index now includes 14 265 cyclic systems
An appendix to the third supplement contains addenda and
corrections to the earlier volumes. The addenda consist
mainly of names and references for new hydro or dehydro
derivatives or for rin systems formerly .known only as
components of c o m p c k d s . The corrections also include
references to better numbering and alternative nomenclature.
The Ring Index needs no special recommendation. I t is so
useful that any volume that carries on the good work must
be regarded as welcome.
H . Griineivtrld
[ N B 511 IE]
CRC Handbook of Chemistry and Physics. Edited by R . C.
Wenst, S . M . Selby, and C . D. Hodgmtrn. The Chemical
Rubber Co., Cleveland, Ohio 1965.46th ed., about 17OOpp..
numerous illustrations, 51 6.00.
The 46th edition of the “Handbook of Chemistry and Physics” contains 200 more pages of tables and other information
than the 45th edition, so that the book now contains more
than 1700 pages and almost 450 tables.
New features include tables on superconductivity, physical
constants of organometallic compounds, the thermal conductivity of gases, the surface tension of liquid elements, and
trade names of dyestuff intermediates. Other tables have
been revised, e.g. the table on buffer solution , but in the
reviewer’s opinion this section is still too brief. For example,
a survey of the buffer solutions commonly used in biochemistry is missing.
Several mathematical tables have been rearranged, so that
they are now vertical instead of harizontal , and there is no
doubt that a new table (23 pages containing every imaginable
conversion factor will he particularly welcome
Special care should be given in future editions to the clear
definition of the data listed in the tables For example, it is not
very significant to give values for the toxicity of gases and
vapors (in ppm or mg,’l) without explaining what has been
taken as the measure of toxicity. I t is also unfortunate that
[“I Cf.
Angew. Chem. 77, 688 (1965): Angew. Chem. internat.
Edit. 4 , 725 (1965).
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