Triazines - Encyclopedia




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TRIAZINES, in organic chemistry, a series of cyclic compounds, containing a ring system composed of three carbon and three nitrogen atoms. Three series are possible, the positions of Marine Trias Of The Alpine And Indian Types.

German Trias.

England.

North Alpine Region.

South Alpine Region.

Alpine Zone

Fo ss il s.

India.

America.

Rhaetic or

Magalodon

Sandstones

P e n a r t h

Kossen Rhaetic Kossen

limestone

and Clays

beds

+'

beds Dachstein beds

and " Hoch-

Star Peak

with Avicula

White Lias,

a ' -'

a Lithoden- Kalk and (Azzarola

Av icula

gebergskalk "

beds

contorta

black pa-

per-shales,

marls

. .-.

a.

A dron Kalk Dolomite

R4

beds)

contorta

in part

Aulacothyris

Sandstones

Bone bed

Bone be

limestone

with dino-

u.

-

Stubensand-

stein

Red and

mottled

-o

?, -

- _ _ _ _ _ - _

c..

Dachstein

_ _ _ _ _ _

Dachstein

Sagenites

beds

s a u r s of

Connecticut

a.

p"

marls with

, o - Li

Kalk and °

o Kalk and

Turbo

Coral lime-

E

rock - salt

,.;?

g,Coral -v

-- Coral

(Worthenia)

stone

a ,

Schilfsand-

stein

-

and gyp-

sum

Variously

coloured

° a,"

?? p

9,E

acts---- -

m limestones a

; d

H

---

a limestones

solitaries

Halorites

beds

H

,..,

a,

a.

' 6 Grenz dolom-

ite

sandstones

and marls

1;3 be

t 1 W

a. Opponitz

a limestone an

Raibl beds

Tropites

subbullatus

Hauerites

beds

..

Taylorville

beds of Cali-

Lettenkohlen-

a sandstein

(with"Wa-

ter-stones

Conglomer-

3 EZ

°

°

.5 Reingrabner

E

beds -a

Trachyceras as

5 iti

p

dolomite

'-

fornia

°' D o l o m i t i c

o limestones

and marls

ate and

breccia

a.

oo

0. tx

j and

Lunz sand- .n

stone

17

' a; c,

0 y. O 0

°

Daonella

beds

Sandstones

with plants,

, x

Haupt- Muschel-

kalk

Anhydrite group,

dolomite and

marls with rock-

salt and gypsum

?,

v

?

=;, o

F +

co

= .a c=

c-)'-~

u

C.)

a Reifling .a U

a, limestone °'

and Part- 'a)

nach beds b

t a, c,

T.; - - -

-o -a ^o Cassian

E :4 ° aa 5 beds

_ a)9 Wengen

? C o beds

W Buchen-

stein

a beds

° - - - - - -

(prezzo lime-

Trachyceras

aon

Daonella

lommeli

lommeli

ras reitzi

Ceratites

trinodosus

Daonella

beds

- - - - -

Ptychites

beds

-

Richmond, ,

Virginia

Koipato beds

Zellendolomit

Wellenkalk an

dolomite

<C

?. 0

9

0 o

cn '-

-a " Alpine a,

Muschel-

a kalk"

ca (part) a

G utten-

stein beds °

° stone)

)

;1 (B rachiopod Z

° a limestone) a

Recoaro

° b limestone a,

o Virgloria o

E - limestone a,

Rhynchonella

decussata

Niti lime-

stone

Hedenstro- a,

emia beds bz

H

a,

-

112eekoceras

beds, Idaho

-

Upper division

Upper mot-

?,, °

Campil beds

Campil beds

Natiria

e

or Roth

Middle division d

or Hauptsand-

stein and (Vos-

tied sand-

stone

Pebble beds

-° ,

.a

,.x

, -a Seis b e d s

.?

S e is beds

costata

Pseudomono-

c ara

Prinolobus

beds

Otoceras °

beds - 0

E-,

o

a

a9 gesensandstein)

Lower division

sandstones with

occasional oolite

(Rogenstein)

Lower mot-

tied sand-

stone

?

x

,4°

x

° v, °

(Permian) .

o-,

v

ct

C02-}-NH3 the various units of the ring system being illustrated in the annexed formulae: C C C NI^C CI C N/C A N ` N' N C,C N N N a-Triazines, (-Triazines, Cyanidines.

Few simple derivatives of the a-series are known, those which have been prepared result by such reactions as the condensation of aminoguanidine or a similar type of compound (e.g. semicarbazide) with ortho-diketones (J. Thiele, Ann., 1898, 302, p. 299): HN:CC NHNH2 OCC 6 H 5 NH N + -> HN:CC CC6 H 5 NH 2 OCC6H5 N = C/-C6H5 Wolff has obtained a chloro-derivative by the action of potassium cyanide on diazoacetophenone and subsequent treatment with acid. The phen-a-triazines are more numerous, and are obtained either by the action of concentrated acids on the formazyl compounds (E. Bamberger, Ber., 1893, 26, p. 2786): CsH5N :N N :N jCCOC6H5 - C6H5NH2+C6H4K C 6 H5NHN N:C0006H5; by the reduction of symmetrical acyl-ortho-nitrophenyl hydrazines (e.g. NO 2 C 6 H 4 NHNHCHO); or in the form of dihydro derivatives by the condensation of aldehydes with ortho-aminoazo compounds (H. Goldschmidt and Y. Rosell, Ber., 1890, 23, p. 487), or from the aminoazo compound and a mustard oil, the resulting thiocarbanilido derivative being heated with acetic acid (M. Busch, Ber., 1899, 32, p. 2960): NC(SH):NC 6 H 5 /NC:NC6H5 C. 2 S 7Hs " H s d-H NNH C,H 7 C7 "NNC,H7 C. Harries (Ber., 1895, 28, p. 1223) has also shown that as-phenylhydrazino-acetic esters, when heated with formamide and substituted formamides under pressure, yield dihydrotriazines: CO 2 R CO-NR'-CH H2N(C6H5)NH2 +R'NHCHO --> CH 2 N(C 6 H 5) IV The phen-a-triazines are yellow-coloured crystalline compounds of a somewhat basic character.

Derivatives of triazines are formed by the action of nitrous acid on ortho-aminobenzylamines (M. Busch, Ber., 1892, 25, p. 445), or in small quantity by the action of nitrous acid on ortho-aminobenzoylphenylhydrazines (A. Konig and A. Reissert, Ber., 18 99, 3 2, p. 782), the chief product in this latter reaction being an isoindazolone: // CH2NHC6H5 /CH2NHC6H5 /CH2NC6H5 C6H4 - C6H4 - C6 H4 NH 2 HCI N :NCI N=N The best drawn series of the triazines is the symmetrical or cyanidine series, members of which result from the condensation of acid anhydrides with aromatic amidines (A. Pinner, Ber., 1892, 25, p. 1624): / NH NC?CsH 5 2C61 - 15 C +(CH 3 C0) 2 0 -> C6H5C N; NH 2 N :C?CH3 or by the condensation of aromatic nitriles with acid chlorides in the presence of aluminium chloride (Eitner and Krafft, Ber., 1892, 25, p. 2263). In using benzoyl chloride in this reaction the condensation is found to proceed better if a little ammonium chloride be added: 2C6H5CNd-C6H5.0001 C6H5 CCl OC C6H5 6 H 5 NC(C6H5):N The cyanidines behave as weak bases.

Mention may be made here of cyanuric acid, H3C3N303, which contains the same ring system as the cyanidines. It was first prepared by C. Scheele and is formed when urea HOC< NC-OH is strongly heated or when cyanuric chloride > N is treated with water. It is usually repre- "N :C -.OH sented by the inset formula and is closely related to cyanic acid and cyamelide, the relationships existing between the three compounds being shown in the diagram (see also A. Hantzsch, Ber., 1906, 39, p. 139): Ordinary temperature Cyamelide (CNOH) 3 Cyanic acid CNOH HO ions 1 High Cyanuric acid Decomposes with temperature

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