thi dicti nary rio to be found on the green pages in either of the - - PDF document

SLIDE 1

• /ution

(e.g. n~~6

.I

: I'e"

at wavelength

0)

ide esonance (data) resonance data persion

I

r an optically

in g/100 g of 1Zine, ligroin)

'urn

n

• f X (e.g.

data

Notes for Users

• I. Introduction

The Beilstein Handbook of Organic Chemistry (Beilsteins Handbuch der Orgo« nischen Chem ie) is a reference work containing information and data r lating to th structure, preparation and properties of organic compounds reported in the primary

• literature. The information is condensed into short entries, each of which record

the important facts and numerical data relating to a particular compound, complete with literature citations, to achieve a very high density of information in the Hand- book. The Handbook is published in several eries, each of which deal with th organic compounds reported in the literature during a given p riod: for each compound there is only one entry within a series . Publication of th Fourth Edition (Vierte Auflage) started in 1918; it consists of the Basic Seri s (Hauptwerk), which cove all the compounds reported up to 1910, and Supplementary ri (Ergdnzungswerke) which cover succeeding periods as indicated in Table 1. Table 1. The Serie of the Beilstein Handbook

v)

>ectro pi pi d ta

lU-

I tiv p

• Volume 17 to 27 of Serie E III and E IV are combin d in a j int i

'i j nt

• • Series H to E IV are bound in brown, Seri

V i b und in blu .

rb

rption

• d

Serie Abbre- viation Literatur Covered Colour of label on

pine··

Langua Basic Series Supplementary Serie Supplementary S ri Suppl m nt ry Seri Suppl mentary S rie Supplementary Serie Supplem ntary eri I

II

III III/IV·

IV V

H EI

Ell

EIII III/IV IV EV

up to 1910

1910-1919 1920-1929 19 0-1 49 1930-1959 1950-1959 1 60-1979

G n

Red Whit Blu

Blu /BI c

BI ck Red Within each erie of the Handbo k th entri Sy tern of ompound Cia ification; thi i a t of rul comp und to be a ign d po ition ithin th Handb i molecular tru tur ; conver ely, knowl d

• f th rul

SLIDE 2

XII

Notes for Users

Within th individual volumes the ordering is based on structural features such as th type and number of functional groups, the degree of unsaturation, the number

• f carbon tom and other similar criteria, until each compo und has been assigned

i

po iti n within the eries. To u e the Handbook effectively, however. it is not

n

ry to no all the rule of the Beilstein System, but merely to be able to

id ntify in which of the 27 volumes the compound is described; this is outlined in th following tion . A more detailed description with worked examples is to be found in the b 0 1 t .. Ho to U e Beilstein" (also available in German) which. t

th r wi h oth r inti rmativ mat rial about the Beilstein Handbook. may be ob-

t in fr f h rg by writing to Beil tein-In titut Springer-Verlag fiir Lit r tur der Organi chen Chemic

• Abt. 4005

Varrentrappstra e 40-42 Tiergartenstrasse 17

0-60

Frankfurt/M. 90 0-6900 Heidelberg I u r of the Beilstein Handbook who are unfamiliar with the German a p cket-size " Beil tein Dictionary" (German/Engli sh) has been compiled

il t in

ditorial staff and i al 0 available free of charge. The contents thi dicti nary rio to be found on the green pages in either of the subvolumes I /IV 22/7 or IV 6/4. 2. tin Compound in the Beilstein Handbook

Th b

t way of finding th ntry for a particular compound in the Beilstein Hand -

book i to identify in which volum

th compound is listed, and then to consult th

appr priat volume inde , d tail of which are given in section 4. In order to

identify th volum of int re t a f ba ic principles of the Beilstein System need to und r tood and the ar d ri d below.

• r th purp
• f cla ification in the B il t in System, all organic compounds

are divid into thr ba ic type, viz. acyclic compounds (Volumes 1-4), isocyclic

(i. . carbocyclic) compound (Volume 5- 16), and heterocyclic compounds (Vol- urn 17 - 27). H t ro yclic compound are furth r subdivided according to the nature

and numb r of th ring heteroatom . All heterocycles containing chalcogen atoms

a th

• nly typ

f ring heteroatom are covered in Volumes 17- 19; those with

• n chalcogcn rin atom (het ro: 1 0) in Volumes 17 and 18, and those with two
• r mor (h tero: 20, 30, ... et .) in Volume 19. Heterocycles containing nitrogen
• a. th only typ of ring heteroatom ar cover din Volum

20-26 ; all other hetero - cyclic comp und , including tho with b th chalcogen and nitrogen ring heteroatoms,

ar d alt with in Vol. 27 (furth r detail

r given in Table 2).

The po ition of the entry for any compound is determined by that fragment of

it

tru tur which i cla iii d late t in th Beil t in Sy t m. Thus, for example,

a comp und

ntaining a h t rocycli ring, a carbocyclic ring and an aliphatic chain

i cl ifi d a a h ter cycl , irre p tiv of th other tructural elements, since all h t rocycl

rd r dafter acycli and i

ycliccompounds in the Beilstein System. Thi f atur of th y tcmatic cla iii tion of compound i called the Principle

• f Lat t

y t mati Entry.

urth r cla ilicati n of compound within th divi i n de cribed above is based upon th typ and number of th

fun tional group which they contain. At this lev I it i n e ary t di tingui h bet n (i) r istry c mpound , and (ii) deri ti

• f r gi try comp und .

SLIDE 3

:- n

n

• 5 · (;; ....

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a

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g 3

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n f P

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• :!..,:rn",::s

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• I»-:::,nO

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• n

3 .., OQ

• s:
• ~'<:

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• ~

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• 0. 0

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Table 2. Registry Co mpounds in the Beilstein Ha ndbook - Volume Numbers. Functional Groups Acyclic Compou nds Isocyclic Co mpounds Heterocyclic compounds Heteroatom : Type and Number (n) Oxygen Only Nitrogen On ly All Other Types of Heterocycle

n=1

n~ 2

n =1

n=2

n ~

3

Compounds Without Functional Groups 5 20 23 26

27

• oH

Hydroxy-Compounds 6

17

Oxo-Compounds 1

7

21 24 =0 Hydroxy-Oxo-Compounds 8 25 Carboxylic Acids 2 9 18 19 22 Carboxylic Acids +Hydroxy- and Oxo-Functions 3 10

• S0 2H.-S0 3H.-Se02H.-Se0 3H.-Te02H

11 Monoamines 12

• NH2

Polyamines and Hydroxy-Amines 13 Amines +Other Functional Groups 14

• N H(OH). - N(OH)2' - NHN H2

4 15

• N=NH. - N=N+ . - NH-N=O. - NH-N0 2•

16 Polynitrogen Functional Groups* Compounds Containing C-M Bonds; M=P, As, Sb, Bi; Si, oe, Sn, Pb; B, Al and Other Metals. z

• ;:;'

en

0' ...

C

en

• ...

en

• Functional groups containing three or more nitrogen atoms, substituted by - H, - OH and =0 only.

x

SLIDE 4

XIV Notes for Users (i) Reg' try compounds are defined as hydrocarbons or heterocycles which bear either no functional groups (i. e. parent compounds), or one or more of the functional groups listed in Table 2, bonded to carbon atoms; no carbon atom, however, may bear more than one functional group *. Three further restrictions apply to heterocyclic rings: the ring must contain at least one carbon atom; ring heteroatom may neither be substituted nor bear functional groups; the ring mu t not contain chalcogen atoms other than oxygen as ring heteroatoms. Compound which do not conform to these criteria are classified as derivatives ( below).

• In carboxylic acid. the functional group consists only of the - OH and =0 groups .

The volum of the Handbook containing the entry for any particular registry corn- und may be id ntified directly from Table 2 on the basis of its skeletal framework nd functional group . For compounds containing two or more different groups, th Principle of Lat t Sy tematic Entry is again applied, and each compound is r th functional group which app ar lowest in the list in Table 2. hydro y­benzen ulfonic acid i cia ified as an isocyclic sulfonic acid not n li hydro y­eompound (Vol. 6). In some cases, e.g. th nd type of functional group is important to determine in th c m und will d aIt with; thu benzene­I,4­diamine (without

• f fun . n I r up) i in Vol. 13, whereas 4­amino­benzoic acid is
• f gi try compound are giv n below:

H I

­c

I

C

l-CO-DH

0t}o H

• III

IV

1

ifi

und

pi,

i.sc:)C}'clic IUUlUl::ll,