107 



ORGANIC BASER 



ORGANIC BASES. 



108 



ning diatomic radical (R") in the place of two 



(C H V 1 

 equivalent! of hydrogen, e.g., oonyUmine (conine) ' "H f ^' 



t. Tertiary monamines containing a diatomic radical, u, for instance, 



( ' H VI 

 methyl-conylamine (methyl-conine) CH" [ N - / Tertiary mona- 



mine* containing a triatomic radical (II ) in the place of three equiva- 

 lent* of hydrogen, example* of them are seen in plcoline (C lt H,)'" j N, 



and leucoline (C,.H.)"' j N. 



2. J>ia*i*a. These bodies are formal upon the type of two atoms 



H,] Hill 



of ammonia, or diaiumonia H. V N,, or H H } N N. A great number 



H,j HHJ 



of organic bases belonging to this type have already been formed ; not 

 only primary, secondary, and tertiary, but belonging to intermediate 

 divisions, the construction of which will be readily understood on 

 looking over the annexed list of the general formula; of diauiines : 



R1I 

 llll 



nil 



XX 



IT I 

 llll [ XX 

 1111 ) 



E- ) 



n" INN 

 RH) 



UK ' XX 



R 

 RR 



RR j 

 111! NX 

 llll ) 



RH } XN 



llll 



R" 

 R" 

 RR 



R~ i 

 R" } NX 



H ) 



RR ) 



KII ' XX 

 llll ) 



R- ) 



RR JNN 

 mi j 



R") 

 R" NN 



R ) 



V 



H 



RR 

 RR 

 llll 



XX 



;'."JNX If'jx.v R | 



R" 



RR 'NX 



i ; 1 1 f 



R" 1 



nn }NN 



H 



NN 



RR) 

 RR NN 

 UII ) 



R" 



KB 

 RK 



XX 



RR) 

 RU } NN 



llll) 



R" ) 

 H" [NN 

 IIU) 



R" 



llll } XX 



H 



R"' 

 RR 

 11 



NX 



"}NN 



The immense number of bodies tliat may be represented by any one 

 of these general formula: may perhaps be obscurely imagined on apply- 

 ing, to either of the first half dozen, the remarks made under the head 

 of secondary monamines. 



The following list of examples of diamines is given in illustration of 

 the above general formukc. Some of the latter, however, have no 

 actually-obtained representatives among the organic bases, although 

 the greater number of them have among the organic neutral principles. 

 [AMIDES.] 



(C,N)H ) (C,N)H ) (C.H..) (C,H 3 ) ) 



XN (o > ,H.)(c I( H ( )Smr (c,n,) (c.n s ) NN 



(C,,H 5 )H j (C.H.,) (C.H 3 ) ) 



Melaniluic. 



Cyao-triphcnyl-diaminc. 



Trimethyl-trivuiTl- 

 diamlnc (Acrtoninc !). 



nn 

 nn 



NX 



Urea. 



(C,H.)H NN 

 H H) 



Ethyl-urea. 



(C.H,,) (C.H S ) 

 H U 



NN 



EthTl.alljrl.urea. 



5(C,.H,)" 

 NN (C' t ll' t )" JNN (C,JI.)" }NN 



(C.A) (CisH.) [ 



Ethjl-pipcrTl-urca. Diethylenc-diphenyl- TiUtilbyl-diamiuc 



diaminc. (Amarinc !). 



(C.H,)"' 



llll JNN (C,,H,)(C M H.)}NN 



NN 



(CJfl 



Acctdlamine. Kormyl-diphcnyl-diaminc. IMnicotyl-diamtnc 



(Conine !). 



A peculiar class of organic bases designated by the term phospha- 

 ninn seem to be diamines, corresponding in constitution to urea. 



(C.SJ" ) 



'.II. I (C.H.) \ NP, Is such a body formed by the action of sulpho- 

 (C.H,)C,-H, ) 



cyanide of phenyl upon triethylphosphine. It contains an equivalent 

 of phosphorus in the place of one of nitrogen. This class has at 

 present only few members, but inasmuch as many monamines exist 

 containing not only phosphorus but arsenic and antimony, in the 

 place of nitrogen, it is possible that the NN in diamines may be 

 replaced by PP, As As, SbSb, and by NAs, NSb, PAs, PSb, and 

 As 8b the same as by NP, as seen in the formula of the phosphamine 

 just given. 



8. Triamina, derived from a triple atom of ammonia or triammonia, 

 The same general remarks that have applied to the monamines and 

 diamines apply also to this third class. Although many natural 

 ' bases contain three equivalents of nitrogen, and may be repre- 

 sented as triauiines, it is not positively known that they really are so, 



and at present only two artificial bases possess the triammonic 

 character at all decidedly ; they are : 



and 



Melamine (tricran-triamine) . 



Cyanclhino (trialljrUrUroinr) 



(C.H.)'" N 

 /i* it \"* I 



4. Tttramine*. Theobromine and caffeine contain four equiv 

 of nitrogen, and may possibly be tetraminos. The only well marked 

 artificial one is glycosine (not glycocin), containing the hypothetical 



,H.>"") 



tetratomic radical glycyl (C.HJ"" ; its formula is (C.H>" 



'" 



its explanatory name would be triglycyl-tetramine. 



. r >. Pentaminei have no representatives among the strictly organic 

 bases. Some cobalt bases that have recently been discovered seem to 

 be pentammonic. 



Ammonium*. When ammonia (NH,) is dissolved in water a solution 

 is obtained having all the characters of the hydrated oxides of tli 

 alkali metals, and is by analogy looked upon, therefore', as containing 



the hydrated oxide of ammonium (NH.O, HO, or H 'H} or 



HHTIHV 1 \ 



u f 0,J. Similarly when the monamines, whose general 



formula) have already been given, are dissolved in water, hydrated 

 oxides of organic bases are produced of the general formula 



RUHH g}o w or KRHH *}o w or HRRH }o,, ^ fc^ the 



termination -monium in place of the original -ine. Thus, ethylamino 

 furnishes hydrated oxide of ethylammonium, and di- and tri-rthvU- 

 mine yield hydrated oxides of di- and tri-ethylammonium. This 

 change of constitution, and therefore of typical expression, is, more- 

 over, warranted by the fact that the fourth equivalent of hydrogen in 

 ammonium may be replaced, and organic bases of the general formula 



,, > 0., readily produced ; such an one is the hydrated oxide of 



ff-i JJ \ W 1 



tetrethylammonium v "5 f Oj, and the corresponding compound 

 of methyl-ethyl-amyl-phenyl-ammouium 



(C,H,) (C.H.) (C 10 H,,) (C la H 5 ) N 

 II 



In the ammoniums, as in the amines, biatomic (R"), teratomic 

 (R"'), and quadratomic (R"") radicals may replace two, three, or 

 four equivalents of hydrogen respectively. There seem also to be 

 compounds conveniently represented on the ammonium type as 

 ammonium in which hydrogen is replaced by ammonium itself, or 

 rather by a derivative of ammonium, but at present only two organic 

 bases can be thus viewed. Finally, there are good indications of the 

 existence of di ammonium and tri-ammonium organic bases <! 

 from double and triple atoms of hydrated oxide of ammonium, and 

 resembling the diamine and triamine bases. 



Formation of Organic bate*. 



The modes hi which the natural organic bases are formed are not 

 yet ascertained, for all attempts to produce them artificially have 

 hitherto foiled. The artificial bases are formed by several processes, 

 which we now propose to notice, including under each a list of the 

 chief bases produced. 



First. Direct substitution of organic radicals for the hydrogen in 

 ammonia. This process will be readily understood by the folv 

 example. A mixture of strong alcoholic solution of ammonia with 

 iodide of ethyl is hermetically sealed up in a long tube and heated for 

 some hours in a water-bath ; combination takes place, and the result 



/C.H. ) \ 



is hydriodate of ethylamino I II > N, HI I. On distilling the latter 

 \ H ) / 



/<'"') \ 

 with potash, iodide of potassium, water, and clfiylamine [ 



\ H ) / 



are formed. On now going through the same process, but u-in.i; 



C.H. ) 

 ethylamine instead of ammonia, dittiiylaminc C.H. > N i obtained. 



On subjecting diethylamine to the same method we produce tr'n lli "/- 



/C.H. ) \ 

 amiiic [ C,H 5 r N 1. Triethylamine unites directly with iodide of 



VCLH. ) / 



ethyl, and the result is the formation of the iodide of tetrothyl- 



C.H.) 



('II f 

 ammonium Q^> N,I= (C.H,). N,I. On now treating this iodide 



with freshly-precipitated oxide of silver, iodide of silver is formed, 

 and the hydrated o.ci<le of tetrethylammoHiiim set free. The latter body 



